JP2016104746A - エストリド基油を調製するための触媒工程 - Google Patents
エストリド基油を調製するための触媒工程 Download PDFInfo
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Abstract
Description
本願は、35 U.S.C.§119(e)の下、2010年8月31日に出願された米国特許仮出願第61/378,891号、並びに2011年6月17日に出願された米国特許仮出願第61/498,499号の利益を主張するものであり、これら双方ともに、全ての目的のためにそれらの全体が参照により本明細書に組み込まれるものとする。
連邦政府委託研究に関する声明
式中、−R64は独立してハロゲンであり、R60及びR61の各々は、独立して、アルキル、置換アルキル、アルコキシ、置換アルコキシ、シクロアルキル、置換シクロアルキル、ヘテロシクロアルキル、置換ヘテロシクロアルキル、アリール、置換アリール、ヘテロアリール、置換ヘテロアリール、アリールアルキル、置換アリールアルキル、ヘテロアリールアルキル、又は置換ヘテロアリールアルキルであるか、若しくはヘテロシクロアルキル、置換ヘテロシクロアルキル、ヘテロアリール又は置換ヘテロアリール環と結合した形態である窒素原子を備えたR60及びR61であり、R62及びR63は、独立して、アルキル、置換アルキル、アリール、置換アリール、アリールアルキル、置換アリールアルキル、シクロアルキル、置換シクロアルキル、ヘテロシクロアルキル、置換ヘテロシクロアルキル、ヘテロアリール、置換ヘテロアリール、ヘテロアリールアルキル、又は置換ヘテロアリールアルキルであるか、若しくは1つ以上のヘテロシクロアルキル、置換ヘテロシクロアルキル、ヘテロアリール、又は置換ヘテロアリール環と結合した形態である原子を備えたR62及びR63であり、
式中、R60、R61、R62、及びR63について上記で定義されたような「置換型」置換基は、アルキル、−アルキル−OH、−O−ハロアルキル、−アルキル−NH2、アルコキシ、シクロアルキル、シクロアルキルアルキル、ヘテロシクロアルキル、ヘテロシクロアルキルアルキル、アリール、ヘテロアリール、アリールアルキル、ヘテロアリールアルキル、−O-、−OH、=O、−O−アルキル、−O−アリール、−O−ヘテロアリールアルキル、−O−シクロアルキル、−O−ヘテロシクロアルキル、-SH、-S-、=S、-S−アルキル、−S−アリール、−S−ヘテロアリールアルキル、−S−シクロアルキル、−S−ヘテロシクロアルキル、−NH2、=NH、−CN、−CF3、−OCN、−SCN、−NO、−NO2、=N2、−N3、−S(O)2O-、−S(O)2、−S(O)2OH、−S(O2)O-、−SO2(アルキル)、−SO2(フェニル)−SO2(ハロアルキル)、−SO2NH2、−SO2NH(アルキル)、−SO2NH(フェニル)、−P(O)(O-)2、−P(O)(O−アルキル)(O-)、OP(O)(O−アルキル)(O−アルキル)、−CO2H、−C(O)O(アルキル)、−CON(アルキル)(アルキル)、−CONH(アルキル)、−CONH2、−C(O)(アルキル)、−C(O)(フェニル)、−C(O)(ハロアルキル)、−OC(O)(アルキル)、−N(アルキル)(アルキル)、−NH(アルキル)、−N(アルキル)(アルキルフェニル)、−NH(アルキルフェニル)、−NHC(O)(アルキル)、−NHC(O)(フェニル)、−N(アルキル)C(O)(アルキル)、及び−N(アルキル)C(O)(フェニル)から独立して選択される2つ又は3つの基などの1つ以上の基に置換されている。
式中、
xは、それぞれの事例に独立して、0、1、2、3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、19、及び20の整数から選択され、
yは、それぞれの事例に独立して、0、1、2、3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、19、及び20の整数から選択され、
nは、1〜12から選択される整数であり、
R1は、飽和又は不飽和の、並びに分岐状又は直鎖状の任意に置換されたアルキルであり、並びに、
R2は、水素、並びに飽和又は不飽和の、及び分岐状又は直鎖状の任意に置換されたアルキルから選択され、
ここにおいて、前記の少なくとも1種の化合物の各々の脂肪酸鎖残基は、独立して任意に置換されている。
式中、
nは、1よりも大きい又は1に等しい整数であり、
R2は、水素、並びに飽和又は不飽和の、及び分岐状又は直鎖状の任意に置換されたアルキルから選択され、
R1、R3、及びR4は、それぞれの事例に独立して、飽和又は不飽和の、並びに分岐状又は直鎖状の任意に置換されたアルキルから選択される。
式中、
xは、それぞれの事例に独立して、0、1、2、3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、19、及び20の整数から選択され、
yは、それぞれの事例に独立して、0、1、2、3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、19、及び20の整数から選択され、
nは、0に等しいか又は0よりも大きく、
R1は、飽和又は不飽和の、並びに分岐状又は直鎖状の任意に置換されたアルキルであり、並びに、
R2は、水素、並びに飽和又は不飽和の、並びに分岐状又は直鎖状の任意に置換されたアルキルから選択され、
ここにおいて、前記の少なくとも1種の化合物の各々の脂肪酸鎖残基は、独立して任意に置換されている。
式中、
nは、1よりも大きい又は1に等しく、
R2は、水素、並びに飽和又は不飽和の、及び分岐状又は直鎖状の任意に置換されたアルキルから選択され、
R1、R3、及びR4は、それぞれの事例に関して独立して、飽和又は不飽和の、並びに分岐状又は直鎖状の任意に置換されたアルキルから選択される。
少なくとも1種の第1の脂肪酸反応体と、少なくとも1種の第2の脂肪酸反応体と、ルイス酸触媒とを提供すること、並びに、 ルイス酸触媒の存在下で、少なくとも第1の脂肪酸反応体を、少なくとも第2の脂肪酸反応体でオリゴマー化して、エストリド化合物及び/又はエストリド組成物を生成することを含む工程によって生成される。
少なくとも1種のカルボン酸反応体と、少なくとも1種のオレフィンと、ビスマス触媒とを提供することと、
ビスマス触媒の存在下で、少なくとも1種のカルボン酸反応体を少なくとも1種のオレフィンと反応させて、カルボン酸エステルを生成すること、とを含む。
実施例
核磁気共鳴:NMRスペクトルは、溶媒として、CDCl3を用いて、300Kで500.113MHzの絶対周波数で、Bruker Avance 500スペクトロメーターを用いて収集した。化学的シフトは、テトラメチルシランからのppmとして報告された。エストリドの形成を示す、脂肪酸の間の二次的なエステルの形成は、約4.84ppmでのピークによって、1H NMRで検証した。
実施例1
実施例2
実施例5
実施例7
実施例9
付記項1.エストリド基油を生成するプロセスであって:
少なくとも1種の第一の脂肪酸反応物質、少なくとも1種の第二の脂肪酸反応物質、及びルイス酸触媒を提供することと、
上記少なくとも1種の第一の脂肪酸反応物質と上記少なくとも1種の第二の脂肪酸反応物質とを、ルイス酸触媒の存在下でオリゴマー形成して、エストリド基油を生成することと、を包含する、プロセス。
少なくとも1種の第一の脂肪酸反応物質、少なくとも1種の第二の脂肪酸反応物質、及びオリゴマー形成触媒を提供することと、
上記少なくとも1種の第一の脂肪酸反応物質と上記少なくとも1種の第二の脂肪酸反応物質とを、オリゴマー形成触媒の存在下で連続的にオリゴマー形成して、エストリド基油を生成することと、を包含する、プロセス。
少なくとも1種のカルボン酸反応物質、少なくとも1種のオレフィン、及びビスマス触媒を提供することと、
上記少なくとも1種のカルボン酸反応物質と上記少なくとも1種のオレフィンとをビスマス触媒の存在下で反応させてカルボン酸エステルを生成することと、
を包含する、プロセス。
Claims (47)
- エストリド基油を生成するためのプロセスであって、
少なくとも1つの不飽和部位を有する少なくとも1種の第一の脂肪酸反応物質、少なくとも1種の第二の脂肪酸反応物質、及びトリフレート触媒を提供することと、
少なくとも1種の第一の脂肪酸反応物質と、少なくとも1種の第二の脂肪酸反応物質とをトリフレート触媒の存在下でオリゴマー形成して、エストリド基油を生成することであって、前記オリゴマー形成は、少なくとも1種の第二の脂肪酸反応物質のカルボキシル基の酸素と、少なくとも1種の第一の脂肪酸反応物質の少なくとも1つの不飽和部位の炭素との間で共有結合を形成することを包含することと、
を包含する、プロセス。 - 前記少なくとも1種の第一の脂肪酸反応物質が、1種以上の不飽和脂肪酸類、又は不飽和脂肪酸オリゴマー類である、請求項1に記載のプロセス。
- 前記少なくとも1種の第二の脂肪酸反応物質が、飽和脂肪酸類、不飽和脂肪酸類、飽和脂肪酸オリゴマー類又は不飽和脂肪酸オリゴマー類の1つ以上である、請求項1及び2のいずれか1項に記載いずれか1項に記載のプロセス。
- 前記トリフレート触媒が、AgOTf、Cu(OTf)2、Fe(OTf)2、Fe(OTf)3、NaOTf、LiOTf、Yb(OTf)3、Y(OTf)3、Zn(OTf)2、Ni(OTf)2、Bi(OTf)3、La(OTf)3又はSc(OTf)3のうち1つ以上である、請求項1〜3のいずれか1項に記載のプロセス。
- 前記トリフレート触媒が、Fe(OTf)3、Bi(OTf)3又はCu(OTf)2の1つ以上である、請求項4に記載のプロセス。
- 前記トリフレート触媒がBi(OTf)3である、請求項4に記載のプロセス。
- 前記トリフレート触媒がCu(OTf)2である、請求項4に記載のプロセス。
- 前記トリフレートがFe(OTf)3である、請求項4に記載のプロセス。
- 前記オリゴマー形成することが、マイクロ波放射線の存在下で生じる、請求項1〜8のいずれか1項に記載のプロセス。
- 前記オリゴマー形成することが、マイクロ波リアクター中で行われる、請求項1〜9のいずれか1項に記載のプロセス。
- 前記オリゴマー形成することがさらに、ブレンステッド酸の存在を含む、請求項1〜10のいずれか1項に記載のプロセス。
- 前記ブレンステッド酸が、塩酸、硝酸、硫酸、リン酸、過塩素酸、トリフリン酸、又はp−TsOHの1つ以上である、請求項11に記載のプロセス。
- 前記ブレンステッド酸が、固体酸である、請求項11に記載のプロセス。
- 前記ブレンステッド酸が、酸活性化白土から選択される、請求項13に記載のプロセス。
- 前記ブレンステッド酸が、酸活性化モントモリロナイト粘土から選択される、請求項13に記載のプロセス。
- 前記ブレンステッド酸が、酸性メソ多孔性材料から選択される、請求項10に記載のプロセス。
- 前記ブレンステッド酸が、ゼオライト材料から選択される、請求項16に記載のプロセス。
- 前記オリゴマー形成することが、50℃を超える温度で行われる、請求項1〜17のいずれか1項に記載のプロセス。
- 前記オリゴマー形成することが、1気圧未満の圧力で行われる、請求項1〜18のいずれか1項に記載のプロセス。
- 前記エストリド基油をエステル化して、エステル化されたエストリド基油を得ることをさらに包含する、請求項1〜19のいずれか1項に記載のプロセス。
- 前記エステル化することが、少なくとも1種のアルコール及び少なくとも1種のエステル化触媒の存在下で行われる、請求項20に記載のプロセス。
- 前記少なくとも1種のエステル化触媒が、ブレンステッド酸エステル化触媒、又はルイス酸エステル化触媒のうち1つ以上である、請求項21に記載のプロセス。
- 前記ブレンステッド酸エステル化触媒が、固体酸を含む、請求項21に記載のプロセス。
- 前記ブレンステッド酸エステル化触媒が、酸活性化白土から選択される、請求項22に記載のプロセス。
- 前記ブレンステッド酸エステル化触媒が、酸活性化モントモリロナイト粘土から選択される、請求項22に記載のプロセス。
- 前記ブレンステッド酸エステル化触媒が、酸性メソ多孔性材料から選択される、請求項22に記載のプロセス。
- 前記ブレンステッド酸エステル化触媒が、ゼオライト材料から選択される、請求項22に記載のプロセス。
- 前記ブレンステッド酸エステル化触媒が、塩酸、スルファミン酸、メチルスルファミン酸、硫酸、硝酸、リン酸、過塩素酸、トリフリン酸、又はp−TsOHの1つ以上である、請求項22に記載のプロセス。
- 前記ルイス酸エステル化触媒がトリフレートである、請求項22に記載のプロセス。
- 前記ルイス酸エステル化触媒が、AgOTf、Cu(OTf)2、Fe(OTf)2、Fe(OTf)3、NaOTf、LiOTf、Yb(OTf)3、Y(OTf)3、Zn(OTf)2、Ni(OTf)2、Bi(OTf)3、La(OTf)3、Sc(OTf)3の1つ以上である、請求項29に記載のプロセス。
- 前記ルイス酸エステル化触媒がBi(OTf)3である、請求項1〜30のいずれか1項に記載のプロセス。
- 前記オリゴマー形成ルイス酸触媒及び前記ルイス酸エステル化触媒が同じである、請求項1〜30のいずれか1項に記載のプロセス。
- 前記ルイス酸エステル化触媒が、少なくとも1種の金属化合物であり、かつチタニウム化合物、スズ化合物、ジルコニウム化合物、又はハフニウム化合物の1つ以上である、請求項22〜30のいずれか1項に記載のプロセス。
- 前記ルイス酸エステル化触媒が、少なくとも1種のチタニウム化合物であり、かつTiCl4、Ti(OCH2CH2CH2CH3)4の1つ以上である、請求項33に記載のプロセス。
- 前記ルイス酸エステル化触媒が、Ti(OCH2CH2CH2CH3)4である、請求項34に記載のプロセス。
- 前記ルイス酸エステル化触媒が、少なくとも1種のスズ化合物であり、かつSn(O2CCO2)、SnO、又はSnCl2の1つ以上である、請求項33に記載のプロセス。
- 前記ルイス酸エステル化触媒が、Sn(O2CCO2)である、請求項36に記載のプロセス。
- 前記ルイス酸エステル化触媒が、少なくとも1種のジルコニウム化合物であり、かつZrCl4、ZrOCl2、ZrO(NO3)2、ZrO(SO4)、又はZrO(CH3COO)2の1つ以上である、請求項33に記載のプロセス。
- 前記ルイス酸エステル化触媒が、ZrOCl2・8H2O及びZrOCl2・2THFから選択される、請求項38に記載のプロセス。
- 前記ルイス酸エステル化触媒が、少なくとも1種のハフニウム化合物であり、かつHfCl2又はHfOCl2の1つ以上である、請求項33に記載のプロセス。
- 前記ルイス酸エステル化触媒が、HfOCl2・2THF及びHfOCl2・8H2Oから選択される、請求項40に記載のプロセス。
- 前記エステル化することが、マイクロ波放射線の存在下で起こる、請求項20〜41のいずれか1項に記載のプロセス。
- 前記エステル化することが、マイクロ波リアクター中で行われる、請求項20〜42のいずれか1項に記載のプロセス。
- 前記プロセスが、連続フロープロセスである、請求項1〜43のいずれか1項に記載のプロセス。
- さらにトリフレート触媒を回収することを包含する、請求項1〜44のいずれか1項に記載のプロセス。
- 前記回収されたトリフレート触媒を再利用することをさらに包含する、請求項45に記載のプロセス。
- 前記回収されたトリフレート触媒が、オリゴマー化のために再利用される、請求項46に記載のプロセス。
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Cited By (2)
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KR20220045209A (ko) | 2019-09-12 | 2022-04-12 | 니혼노야쿠가부시키가이샤 | 치환 시클로프로판옥사디아졸기를 갖는 축합 복소환 화합물 또는 이의 염류를 유효성분으로 하는 농원예용 살충제 또는 동물용의 외부 혹은 내부 기생충 방제제 및 이의 사용 방법 |
KR20220047320A (ko) | 2019-09-12 | 2022-04-15 | 니혼노야쿠가부시키가이샤 | 치환 시클로프로판옥사디아졸기를 갖는 이미다조피리다진 화합물 또는 이의 염류를 유효성분으로 하는 농원예용 살충제 또는 동물용의 외부 혹은 내부 기생충 방제제 및 이의 사용 방법 |
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