JPS623826B2 - - Google Patents
Info
- Publication number
- JPS623826B2 JPS623826B2 JP7256979A JP7256979A JPS623826B2 JP S623826 B2 JPS623826 B2 JP S623826B2 JP 7256979 A JP7256979 A JP 7256979A JP 7256979 A JP7256979 A JP 7256979A JP S623826 B2 JPS623826 B2 JP S623826B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- compound according
- group
- chain alkyl
- alkyl group
- 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.)
- Expired
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- 150000001875 compounds Chemical class 0.000 claims description 29
- -1 n-octyl group Chemical group 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- OWCLRJQYKBAMOL-UHFFFAOYSA-N 2-butyloctanedioic acid Chemical class CCCCC(C(O)=O)CCCCCC(O)=O OWCLRJQYKBAMOL-UHFFFAOYSA-N 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000004927 clay Substances 0.000 description 5
- 238000007127 saponification reaction Methods 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XWBRIBOOHPSRFU-UHFFFAOYSA-N CCCCC(CCCCCC(=O)OC(C)C)C(=O)OC(C)C Chemical compound CCCCC(CCCCCC(=O)OC(C)C)C(=O)OC(C)C XWBRIBOOHPSRFU-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- OIINNURLJDFBNL-UHFFFAOYSA-N diethyl 2-butyloctanedioate Chemical compound CCCCC(C(=O)OCC)CCCCCC(=O)OCC OIINNURLJDFBNL-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- SOYRWPZPGGHTQR-UHFFFAOYSA-N CCCCC(CCCCCC(=O)OC(C)CC)C(=O)OC(C)CC Chemical compound CCCCC(CCCCCC(=O)OC(C)CC)C(=O)OC(C)CC SOYRWPZPGGHTQR-UHFFFAOYSA-N 0.000 description 1
- RRHQFBADNBPRPL-UHFFFAOYSA-N CCCCOC(=O)CCCCCC(CCCC)C(=O)OCCCC Chemical compound CCCCOC(=O)CCCCCC(CCCC)C(=O)OCCCC RRHQFBADNBPRPL-UHFFFAOYSA-N 0.000 description 1
- FNOSGJZQRNMXRO-UHFFFAOYSA-N CCCOC(=O)C(CCCC)CCCCCC(=O)OCCC Chemical compound CCCOC(=O)C(CCCC)CCCCCC(=O)OCCC FNOSGJZQRNMXRO-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- 239000012080 ambient air Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical compound [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
Description
【発明の詳細な説明】
本発明は化粧品、医薬品、工業用等の油剤また
は乳剤等の基剤として有用なる文献未知の新規な
２−ブチルオクタン二酸エステル類に関するもの
である。さらに詳しくは、本発明は一般式（）
（式中Ｒは炭素数２以上の直鎖アルキル基、直鎖
アルケニル基およびヒドロキシアルキル基をある
いは炭素数３以上の側鎖アルキル基を表わす）で
示される２−ブチルオクタン二酸エステル類に関
するものである。本発明で得られる化合物は例え
ば次のようなものである。２−ブチルオクタン二
酸ジエチルエステル、２−ブチルオクタン二酸ジ
プロピルエステル、２−ブチルオクタン二酸ジブ
チルエステル、２−ブチルオクタン二酸ジベンチ
ルエステル、２−ブチルオクタン二酸ジヘキシル
エステル、２−ブチルオクタン二酸ジオクチルエ
ステル、２−ブチルオクタン二酸ジデシルエステ
ル、２−ブチルオクタン二酸ジラウリルエステ
ル、２−ブチルオクタン二酸ジテトラデシルエス
テル、２−ブチルオクタン二酸ジヘキサデシルエ
ステル、２−ブチルオクタン二酸ジオクタデシル
エステル、２−ブチルオクタン二酸ジオレイルエ
ステル、２−ブチオクタン二酸ジイソプロピルエ
ステル、２−ブチルオクタン二酸ジイテブチルエ
ステル、２−ブチルオクタン二酸ジ−secブチル
エステル、２−ブチルオクタン二酸ジ−（３−メ
チルブチル）エステル、２−ブチルオクタン二酸
ジ−（２−エチルヘキシル）エステル、２−ブチ
ルオクタン二酸ジ（２−オクチルドデシル）エス
テル、２−ブチルオクタン二酸ジ（12−ヒドロキ
シオクタデシル）エステル等である。一般式
（）で示される本発明の化合物は例えば次のよ
うにして製造することが出来る。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel 2-butyloctane dioic acid esters, unknown in the literature, which are useful as bases for oils or emulsions for cosmetics, pharmaceuticals, industrial use, etc. More specifically, the present invention relates to the general formula () (In the formula, R represents a straight-chain alkyl group, a straight-chain alkenyl group, or a hydroxyalkyl group having 2 or more carbon atoms, or a side-chain alkyl group having 3 or more carbon atoms.) It is. Examples of the compounds obtained in the present invention are as follows. 2-Butyloctanedioic acid diethyl ester, 2-butyloctanedioic acid dipropyl ester, 2-butyloctanedioic acid dibutyl ester, 2-butyloctanedioic acid dibenthyl ester, 2-butyloctanedioic acid dihexyl ester, 2-butyl octanedioic acid dioctyl ester, 2-butyloctanedioic acid didecyl ester, 2-butyloctanedioic acid dilauryl ester, 2-butyloctanedioic acid ditetradecyl ester, 2-butyloctanedioic acid dihexadecyl ester, 2- Butyloctanedioic acid dioctadecyl ester, 2-butyloctanedioic acid dioleyl ester, 2-butyloctanedioic acid diisopropyl ester, 2-butyloctanedioic acid diitebutyl ester, 2-butyloctanedioic acid di-sec butyl ester, 2 -Butyloctanedioic acid di-(3-methylbutyl) ester, 2-butyloctanedioic acid di-(2-ethylhexyl) ester, 2-butyloctanedioic acid di(2-octyldodecyl) ester, 2-butyloctanedioic acid Di(12-hydroxyoctadecyl) ester and the like. The compound of the present invention represented by the general formula () can be produced, for example, as follows.
式（）
で表わされるジカルボン酸あるいは化合物（）
反応性誘導体と炭素数２以上の直鎖アルコールお
よび炭素数３以上の側鎖アルコールあるいは、上
記アルコール類の反応性誘導体と反応させること
により容易に目的とする一般式（）で示される
エステル類が得られる。例えば工業的には式
（）のジカルボン酸と上記のアルコール類とを
200〜250゜で４〜15時間程度加熱を行なうか、あ
るいは硫酸のような鉱酸あるいはパラートエンス
ルホン酸のようなベンゼンスルホン酸類の脱水剤
の下で、式（）ジカルボン酸と上記のアルコー
ル類を反応させてもよい。上記の反応は窒素ガス
や炭酸ガスのような不活性ガス気流下で行なつた
方が着色の防止にもつながるので製品の純度の面
から考慮すると好ましい結果が得られる。また着
色した場合は活性炭か活性白土で処理するとよい
結果が得られる。さらに高純度のものを必要とす
る場合は、式（）のジカルボン酸の反応性誘導
体例えば臭化チオニル、塩化チオニル等のハロゲ
ン化剤で（）のジブロマイド、あるいはジクロ
ライドとなしこれに上記のアルコール類をトリエ
チルアミン、ピリジン等の塩基性触媒下で反応さ
せることにより高収率で得られる。さらにカラム
クロマトグラフイー等で処理すれば高純度の目的
物のジエステルが得られる。また（）のナトリ
ウム塩、カルシウム塩等の金属塩と上記アルコー
ル類のハロゲン体を反応させてもよい。もちろん
上記以外の他の公知のエステル化法でも製造可能
である。本発明の化合物はすべて文献未知の新規
化合物であり化粧品や医薬品の外用基剤として優
れた特徴を有している。例えば熱、光、温度等に
対する安定性がよく医薬品や化粧品等の基剤とし
て用いるためには重要な要素の一つである物理
的、化学的安定性に優れている点、また無味、無
臭、無色であり非常に使用しやすくさらに皮膚刺
激が非常にすくなく基剤として従来のこの系統の
ものにみられなかつたいろいろな優れた特徴を有
している。又本化合物類は可塑剤、合成潤滑油な
どの工業用油剤としてもすぐれた性質を有してい
る。本発明の化合物類（）は一般に水に難溶で
アルコール等の有機溶媒に可溶である。本物質類
は化合物の種類により油状のものペースト状のも
のワツクス状のものが存在するのでその用途によ
りいろいろ使い分けが可能でありまた組合せて特
徴のある基剤として用いられることもできる。以
下に実施例にて本発明を説明するがこれに限定さ
れるものではない。 formula() Dicarboxylic acid or compound represented by ()
By reacting the reactive derivative with a linear alcohol having 2 or more carbon atoms, a side chain alcohol having 3 or more carbon atoms, or a reactive derivative of the above-mentioned alcohols, the desired esters represented by the general formula () can be easily obtained. can get. For example, industrially, the dicarboxylic acid of formula () and the above alcohols are
The dicarboxylic acid of formula () and the above alcohol are heated at 200 to 250 degrees for about 4 to 15 hours, or under a dehydrating agent such as a mineral acid such as sulfuric acid or a benzenesulfonic acid such as paratoenesulfonic acid. may be reacted. It is better to carry out the above reaction under a flow of an inert gas such as nitrogen gas or carbon dioxide gas to prevent coloring, and thus to obtain a preferable result from the viewpoint of product purity. If it is colored, good results can be obtained by treating it with activated carbon or activated clay. If even higher purity is required, a reactive derivative of the dicarboxylic acid of the formula () may be used with a halogenating agent such as thionyl bromide or thionyl chloride to form the dibromide or dichloride of the formula (). can be obtained in high yield by reacting them under a basic catalyst such as triethylamine or pyridine. Further treatment with column chromatography etc. yields the target diester with high purity. Alternatively, metal salts such as sodium salts and calcium salts of () may be reacted with halogenated alcohols. Of course, other known esterification methods other than those described above can also be used. The compounds of the present invention are all novel compounds unknown in the literature and have excellent characteristics as external bases for cosmetics and pharmaceuticals. For example, it has good stability against heat, light, temperature, etc., and has excellent physical and chemical stability, which is an important element for use as a base for pharmaceuticals and cosmetics. It is colorless, very easy to use, causes very little skin irritation, and has various excellent characteristics as a base that have not been seen in conventional products of this type. The present compounds also have excellent properties as plasticizers and industrial oils such as synthetic lubricants. The compounds () of the present invention are generally sparingly soluble in water and soluble in organic solvents such as alcohol. These substances can be used in various forms depending on the type of compound, such as oil, paste, or wax, and can be used in various ways depending on the intended use, and can also be used in combination as a unique base. The present invention will be explained below with reference to Examples, but the present invention is not limited thereto.
実施例 １
２−ブチルオクタン二酸ジエチルエステルの製
造法
２−ブチルオクタン二酸2.3ｇとエタノール50
mlを混合し乾燥塩化水素ガスを導入しながら３時
間加熱還流させる。反応終了後過剰のエタノール
を留去し、残留物に冷却下10％NaHCO3水を加え
て中和しエーテル抽出、エーテルは１回水洗後
Na2SO4で乾燥し、エーテルを留去すれば無色の
液体のジエチルエステル体2.2ｇが得られる。Example 1 Method for producing 2-butyloctanedioic acid diethyl ester 2.3 g of 2-butyloctanedioic acid and 50 ml of ethanol
ml and heated under reflux for 3 hours while introducing dry hydrogen chloride gas. After the reaction, excess ethanol was distilled off, and the residue was neutralized by adding 10% NaHCO 3 water under cooling, and extracted with ether. The ether was washed once with water.
Drying with Na 2 SO 4 and distilling off the ether gives 2.2 g of diethyl ester as a colorless liquid.
実施例 ２
２−ブチルオクタン二酸ジヘキシルエステルの
製造法
２−ブチルオクタン二酸2.3ｇとヘキシルアル
コール2.1ｇを混合し濃H2SO4を触媒程度加え５
時間80〜100゜で加熱撹拌を行う。反応終了後冷
却下10％NaHCO3水で中和しエーテル抽出、
Na2SO4で乾燥後溶媒を留去すればジヘキシルエ
ステルを淡黄色油状物として3.5ｇが得られる。Example 2 Method for producing 2-butyloctanedioic acid dihexyl ester 2.3 g of 2-butyloctanedioic acid and 2.1 g of hexyl alcohol were mixed, and concentrated H 2 SO 4 was added to a catalytic level.
Heat and stir at 80-100° for an hour. After the reaction is complete, neutralize with 10% NaHCO3 water under cooling and extract with ether.
After drying with Na 2 SO 4 and distilling off the solvent, 3.5 g of dihexyl ester was obtained as a pale yellow oil.
実施例 ３
２−ブチルオクタン二酸ジデシルエステルの製
造法
２−ブチルオクタン二酸2.3ｇとデシルアルコ
ール3.2ｇを混合しチツソ分囲気下230〜240゜で
約８時間加熱撹拌を行なうと目的とするジデルエ
ステルが淡黄色ペースト状のものとして4.7ｇの
収量で得られる。。収量91.4％
物性値：酸価2.5
：水酸基価1.9
：ケン化価21.9
実施例 ４
２−ブチルオクタン二酸ジオクタデシルエステ
ルの製造法
２−ブチルオクタン二酸2.3ｇとステアリルア
ルコール5.4ｇを混合しチツソ分囲気下230〜240
゜で約５時間加熱撹拌を行なうと目的とするジオ
クタデシルエステル体として6.9ｇが得られる。
このものは活性炭か活性白土で処理を行なえば白
色のワツクス状のものとして得られる。Example 3 Method for producing 2-butyloctanedioic acid didecyl ester 2.3 g of 2-butyloctanedioic acid and 3.2 g of decyl alcohol were mixed and heated and stirred at 230 to 240° for about 8 hours under a Chituso atmosphere to achieve the desired result. A yield of 4.7 g of the didel ester was obtained as a pale yellow paste. . Yield 91.4% Physical properties: acid value 2.5 : hydroxyl value 1.9 : saponification value 21.9 Example 4 Method for producing 2-butyloctanedioic acid dioctadecyl ester 2.3 g of 2-butyloctanedioic acid and 5.4 g of stearyl alcohol were mixed and 230～240
When heated and stirred at 30°C for about 5 hours, 6.9g of the desired dioctadecyl ester was obtained.
This product can be obtained as a white wax-like product by treating it with activated carbon or activated clay.
酸化4.0、水酸基価4.7、ケン化価156.0
実施例 ５
２−ブチルオクタン二酸ジイソプロピルエステ
ルの製造法
２−ブチルオクタン二酸５ｇとイソプロパノー
ル20ｇをベンゼン50ｇに溶解しこれにパラトルエ
ンスルホン酸0.1ｇを加えその混合物を約40時間
加熱還流させる。その間生成する水をときどき共
沸混合物として留去させる。イソプロパノールと
ベンゼンは留去させた分だけ補う。反応終了後イ
ソプロパノールおよびベンゼンを常圧で留去した
後、残査を２回温水で洗いついで希アルカルで中
和し、つづいて温水で洗滌し脱水後減圧蒸留を行
なう。沸点３mmHgで150〜155゜の留分を集め
る。 Oxidation value: 4.0, hydroxyl value: 4.7, saponification value: 156.0 Example 5 Method for producing 2-butyloctanedioic acid diisopropyl ester 5 g of 2-butyloctanedioic acid and 20 g of isopropanol were dissolved in 50 g of benzene, and 0.1 g of para-toluenesulfonic acid was dissolved therein. and the mixture is heated to reflux for about 40 hours. The water formed during this time is sometimes distilled off as an azeotrope. Make up for isopropanol and benzene by the amount that was distilled off. After the reaction is completed, isopropanol and benzene are distilled off at normal pressure, and the residue is washed twice with warm water, neutralized with dilute alkal, then washed with warm water, dehydrated, and then distilled under reduced pressure. Collect the fraction with a boiling point of 3 mmHg and a temperature of 150 to 155°.
収量３ｇ、酸価0.4、ケン化価356（無色透明液
体）
実施例 ６
２−ブチルオクタン二酸ジ−２−オクチルドデ
シルエステルの製造法
２−ブチルオクタン二酸2.3ｇと２−オクチル
ドデカノール6.3ｇを混合しチツソ分囲気下230〜
250゜で約10時間加熱撹拌を行なうと目的とする
ジオクチルドデシルエステル体として7.6ｇが得
られる。このものは活性炭か活性白土で処理を行
なえば無色の油状物として得られる。 Yield 3g, acid value 0.4, saponification value 356 (colorless transparent liquid) Example 6 Method for producing 2-butyloctanedioic acid di-2-octyldodecyl ester 2-butyloctanedioic acid 2.3g and 2-octyldodecanol 6.3g Mix 230 g under the ambient air
By heating and stirring at 250° for about 10 hours, 7.6 g of the desired dioctyl dodecyl ester is obtained. This substance is obtained as a colorless oil by treatment with activated carbon or activated clay.
物性値：酸価2.3
：水酸基価4.2
：ケン化価143
実施例 ７
２−ブチルオクタン二酸ジオレイルエステルの
製造法
２−ブチルオクタン二酸2.3ｇとオレイルアル
コール5.4ｇを混合しチツソ分囲気下230〜240゜
で約５時間加熱撹拌を行なうと、目的とするジオ
レイルエステル体として7.1ｇが得られる。この
ものは活性炭か活性白土で処理を行なえば無色の
油状物として得られる。Physical property values: acid value 2.3: hydroxyl value 4.2: saponification value 143 Example 7 Method for producing 2-butyloctanedioic acid dioleyl ester 2.3 g of 2-butyloctanedioic acid and 5.4 g of oleyl alcohol were mixed and heated under a Chituso atmosphere. By heating and stirring at 230-240° for about 5 hours, 7.1 g of the desired dioleyl ester is obtained. This substance is obtained as a colorless oil by treatment with activated carbon or activated clay.
酸価3.1、水酸基価5.2、ケン化価151.0、ヨウ素
価66.7
実施例 ８
２−ブチルオクタン二酸ジ−12−ヒドロキシオ
クタデシルエステルの製造法
２−ブチルオクタン二酸2.3ｇと12ヒドロキシ
オクタデシアルコール5.7ｇを混合しチツソ分囲
気下230〜240゜で５時間加熱撹拌行なうと、目的
とするジ−12−ヒドロキシオクタデシルエステル
体として7.3ｇが得られる。このものは活性炭か
活性白土で処理を行なえば白色のペースト状のも
のとして得られる。 Acid value 3.1, hydroxyl value 5.2, saponification value 151.0, iodine value 66.7 Example 8 Method for producing 2-butyloctanedioic acid di-12-hydroxyoctadecyl ester 2-butyloctanedioic acid 2.3 g and 12-hydroxyoctadecyl alcohol 5.7 When the mixture is heated and stirred at 230 to 240° for 5 hours under an atmosphere similar to that of Chitsuso, 7.3 g of the desired di-12-hydroxyoctadecyl ester is obtained. This material can be obtained as a white paste by treating it with activated carbon or activated clay.
Claims (1)
基および直鎖アルケニル基およびヒドロキシアル
キル基をあるいは炭素数３以上の側鎖アルキル基
を表わす）で示される２−ブチルオクタン二酸エ
ステル類。 ２ 一般式（）のＲがエチル基である特許請求
の範囲第１項記載の化合物。 ３ 一般式（）のＲがｎ−プロピル基である特
許請求の範囲第１項記載の化合物。 ４ 一般式（）のＲがｎ−ブチル基である特許
請求の範囲第１項記載の化合物。 ５ 一般式（）のＲがｎ−ペンチル基である特
許請求の範囲第１項記載の化合物。 ６ 一般式（）のＲがｎ−ヘキシル基である特
許請求の範囲第１項記載の化合物。 ７ 一般式（）のＲがｎ−オクチル基である特
許請求の範囲第１項記載の化合物。 ８ 一般式（）のＲが炭素数10の直鎖アルキル
基である特許請求の範囲第１項記載の化合物。 ９ 一般式（）のＲが炭素数12の直鎖アルキル
基である特許請求の範囲第１項記載の化合物。 １０ 一般式（）のＲが炭素数14の直鎖アルキ
ル基である特許請求の範囲第１項記載の化合物。 １１ 一般式（）のＲが炭素数16の直鎖アルキ
ル基である特許請求の範囲第１項記載の化合物。 １２ 一般式（）のＲが炭素数18の直鎖アルキ
ル基である特許請求の範囲第１項記載の化合物。 １３ 一般式（）のＲが炭素数18の直鎖アルケ
ニル基で直鎖アルケニル基の９〜10位に二重結合
を有する特許請求の範囲第１項記載の化合物。 １４ 一般式（）のＲの側鎖アルキル基がイソ
プロピル基である特許請求の範囲第１項記載の化
合物。 １５ 一般式（）のＲがイソブチル基である特
許請求の範囲第１項記載の化合物。 １６ 一般式（）のＲがsec−ブチル基である
特許請求の範囲第１項記載の化合物。 １７ 一般式（）のＲが３−メチルブチル基で
ある特許請求の範囲第１項記載の化合物。 １８ 一般式（）のＲが２−エチルヘキシル基
である特許請求の範囲第１項記載の化合物。 １９ 一般式（）のＲの側鎖アルキル基が２−
オクチルドデシル基である特許請求の範囲第１項
記載の化合物。 ２０ 一般式（）のＲが炭素数16の側鎖アルキ
ル基である特許請求の範囲第１項記載の化合物。 ２１ 一般式（）のＲの側鎖アルキル基がイソ
ステアリル基である特許請求の範囲第１項記載の
化合物。 ２２ 一般式（）のＲが炭素数18の直鎖アルキ
ル基で、直鎖アルキル基の12位に水酸基を有する
特許請求の範囲第１項記載の化合物。[Claims] 1 General formula () (However, in the formula, R represents a straight chain alkyl group having 2 or more carbon atoms, a straight chain alkenyl group, a hydroxyalkyl group, or a side chain alkyl group having 3 or more carbon atoms) 2-butyloctanedioic acid esters . 2. The compound according to claim 1, wherein R in the general formula () is an ethyl group. 3. The compound according to claim 1, wherein R in the general formula () is an n-propyl group. 4. The compound according to claim 1, wherein R in the general formula () is an n-butyl group. 5. The compound according to claim 1, wherein R in the general formula () is an n-pentyl group. 6. The compound according to claim 1, wherein R in the general formula () is an n-hexyl group. 7. The compound according to claim 1, wherein R in the general formula () is an n-octyl group. 8. The compound according to claim 1, wherein R in the general formula () is a straight-chain alkyl group having 10 carbon atoms. 9. The compound according to claim 1, wherein R in the general formula () is a straight-chain alkyl group having 12 carbon atoms. 10. The compound according to claim 1, wherein R in the general formula () is a straight-chain alkyl group having 14 carbon atoms. 11. The compound according to claim 1, wherein R in the general formula () is a straight-chain alkyl group having 16 carbon atoms. 12. The compound according to claim 1, wherein R in the general formula () is a straight-chain alkyl group having 18 carbon atoms. 13. The compound according to claim 1, wherein R in the general formula () is a linear alkenyl group having 18 carbon atoms and has a double bond at the 9th to 10th positions of the linear alkenyl group. 14. The compound according to claim 1, wherein the side chain alkyl group of R in the general formula () is an isopropyl group. 15. The compound according to claim 1, wherein R in the general formula () is an isobutyl group. 16. The compound according to claim 1, wherein R in the general formula () is a sec-butyl group. 17. The compound according to claim 1, wherein R in the general formula () is a 3-methylbutyl group. 18. The compound according to claim 1, wherein R in the general formula () is a 2-ethylhexyl group. 19 The side chain alkyl group of R in the general formula () is 2-
The compound according to claim 1, which is an octyldodecyl group. 20. The compound according to claim 1, wherein R in the general formula () is a side chain alkyl group having 16 carbon atoms. 21. The compound according to claim 1, wherein the side chain alkyl group of R in the general formula () is an isostearyl group. 22. The compound according to claim 1, wherein R in the general formula () is a straight chain alkyl group having 18 carbon atoms, and the straight chain alkyl group has a hydroxyl group at the 12th position.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7256979A JPS55164656A (en) | 1979-06-09 | 1979-06-09 | Ester of 2-butyl-octadioic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7256979A JPS55164656A (en) | 1979-06-09 | 1979-06-09 | Ester of 2-butyl-octadioic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55164656A JPS55164656A (en) | 1980-12-22 |
| JPS623826B2 true JPS623826B2 (en) | 1987-01-27 |
Family
ID=13493124
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7256979A Granted JPS55164656A (en) | 1979-06-09 | 1979-06-09 | Ester of 2-butyl-octadioic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS55164656A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2009057427A1 (en) * | 2007-10-29 | 2011-03-10 | 宇部興産株式会社 | Secondary carboxylic acid compound and electrolytic solution for electrolytic capacitor using the same |
-
1979
- 1979-06-09 JP JP7256979A patent/JPS55164656A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55164656A (en) | 1980-12-22 |
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