JP2015509912A - 塩素化プロパン及びプロペンの製造方法 - Google Patents
塩素化プロパン及びプロペンの製造方法 Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/013—Preparation of halogenated hydrocarbons by addition of halogens
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/23—Preparation of halogenated hydrocarbons by dehalogenation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
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Abstract
Description
レギオ選択性触媒として塩化アルミニウムと、塩素化剤として塩化スルフリルを用いる、トリクロロプロパンへのPDCのイオン性塩素化。
レギオ選択性触媒として塩化アルミニウムと、塩素化剤として塩化スルフリルを用いる、1,1,2,2,3−ペンタクロロプロパンへの1,2−ジクロロプロパンのイオン性塩素化。
レギオ選択性触媒としてヨードベンゼン及び塩化アルミニウムと、塩素化剤として塩化スルフリルを用いる、1,1,2,2,3−ペンタクロロプロパンへの1,1,2−トリクロロプロパンの塩素化。
レギオ選択性触媒として、ヨードデュレン(2,3,5,6−テトラメチル−1−ヨードベンゼン)及び塩化アルミニウムと、塩素化剤として塩化スルフリルを用いる、1,1,2,2,3−ペンタクロロプロパンへの1,1,2−トリクロロプロパンの塩素化。
レギオ選択性触媒として、過ヨウ素酸ナトリウム及び塩化アルミニウムと、塩素化剤として塩化スルフリルを用いる、1,1,2,2,3−ペンタクロロプロパンへの1,2−ジクロロプロパンの塩素化。
レギオ選択性触媒として塩化アルミニウム及び回収した過ヨウ素酸ナトリウムと、塩素化剤として塩化スルフリルを用いる、1,1,2,2,3−ペンタクロロプロパンへの1,2−ジクロロプロパンの塩素化。
レギオ選択性触媒としてヨウ素酸ナトリウム及び塩化アルミニウムと、塩素化剤として塩化スルフリルを用いる、1,1,2,2,3−ペンタクロロプロパンへの1,2−ジクロロプロパンの塩素化。
レギオ選択性触媒としてヨウ素酸ナトリウム及び塩化アルミニウムと、塩素化剤として塩化スルフリルを用いる、1,1,2,2,3−ペンタクロロプロパンへの1,2−ジクロロプロパンの塩素化。
レギオ選択性触媒として塩化アルミニウムと、塩素化剤として塩素を用いる、1,1,2,2,3−ペンタクロロプロパンへの1,2−ジクロロプロパンの塩素化。1,2−ジクロロプロパン(10mL)を、三塩化アルミニウム(0.51g)を含有する四塩化炭素(37.2mL)の溶液に添加する。混合物を攪拌しつつ、塩素(30% v/v 窒素中)を溶液に通すのと同時に、混合物を50℃で3時間、次いで100℃で1時間保持する。システムの圧力を反応全体にわたり60〜100psigの間に維持した。1H NMR分光法による反応混合物の分析は、1,2−ジクロロプロパンが50℃で3時間のうちにほぼ消費され、主生成物として、1,1,2−トリクロロプロパンを生成したことを明らかにした。更に100℃で1時間後、最終混合物の分析で、主生成物として1,1,2,2,3−ペンタクロロプロパンを同定した。
レギオ選択性触媒として塩化アルミニウム及び低レベルの元素状ヨウ素と、塩素化剤として塩素を用いる、1,1,2,2,3−ペンタクロロプロパンへの1,2−ジクロロプロパンの塩素化。
[項目1]
1,2−ジクロロプロパンを含む供給流からの塩素化プロパン及び/又はプロペンの製造方法であって、一つのクロロプロパン対他のクロロプロパンが少なくとも5:1となるレギオ選択性を提供する、一又は複数のレギオ選択性触媒で少なくとも一つの塩素化段階を触媒する工程を含む、方法。
[項目2]
前記レギオ選択性触媒が、塩化アルミニウムを含む、項目1に記載の方法。
[項目3]
前記レギオ選択性触媒が、非金属ヨウ化物、無機ヨード塩、又は10,000ppm未満の元素状ヨウ素を含む、項目1に記載の方法。
[項目4]
前記レギオ選択性触媒が、一又は複数のヨードベンゼン又はハロゲン化ヨードベンゼン、フェニルクロロヨードニウムクロリド、ジアリールヨードニウム塩、ヨウ素化ポリマー、ヨードキシ化合物、ヨードソ化合物、モノ及び三ハロゲン化ヨウ素、ヨウ素酸化物、及び任意の数のこれらの誘導体又は組み合わせを含む非金属ヨウ化物を含んでなる、項目3に記載の方法。
[項目5]
前記レギオ選択性触媒が、ヨウ素酸ナトリウム、過ヨウ素酸ナトリウム、又はこれらの組み合わせを含む無機ヨード塩を含んでなる、項目3に記載の方法。
[項目6]
少なくとも二つの塩素化段階を前記レギオ選択性触媒で触媒する、項目1に記載の方法。
[項目7]
一つの塩素化段階を塩化アルミニウムで触媒し、別の段階を非金属ヨウ化物、無機ヨード塩又は10,000ppm未満の元素状ヨウ素で触媒する、項目6に記載の方法。
[項目8]
両段階を同じ反応器内で行う、項目7に記載の方法。
[項目9]
少なくとも一つの塩素化段階を、フリーラジカル開始剤又はイオン性塩素化触媒の存在下で行い、前記フリーラジカル開始剤が、アゾビスイソブチロニトリル、1,1’−アゾビス(シクロヘキサンカルボニトリル)、ジ−tert−ブチルペルオキシド、過酸化ベンゾイル、過酸化ジベンゾイル、過酸化メチルエチルケトン、過酸化アセトン、又は任意の数のこれらの組み合わせを含む、項目1に記載の方法。
[項目10]
少なくとも一つの脱塩化水素段階を更に含む、項目1に記載の方法。
[項目11]
前記少なくとも一つの脱塩化水素段階を触媒の存在下で行う、項目10に記載の方法。
[項目12]
塩素原子源が、塩化スルフリル、塩素又はこれらの組み合わせ、のいずれかを含む、項目1に記載の方法。
[項目13]
前記方法を、更に、四塩化炭素及び/又は塩化スルフリルを含む溶媒の存在下で行う、項目12に記載の方法。
[項目14]
前記一つのクロロプロパンが、1,1,2−トリクロロプロパン、1,1,2,2,3−ペンタクロロプロパン又はこれらの組み合わせを含むトリ−、又はペンタクロロプロパンである、項目1に記載の方法。
[項目15]
前記塩素化プロペンが、1,1,2,3−テトラクロロプロペンを含む、項目1に記載の方法。
Claims (15)
- 1,2−ジクロロプロパンを含む供給流からの塩素化プロパン及び/又はプロペンの製造方法であって、一つのクロロプロパン対他のクロロプロパンが少なくとも5:1となるレギオ選択性を提供する、一又は複数のレギオ選択性触媒で少なくとも一つの塩素化段階を触媒する工程を含む、方法。
- 前記レギオ選択性触媒が、塩化アルミニウムを含む、請求項1に記載の方法。
- 前記レギオ選択性触媒が、非金属ヨウ化物、無機ヨード塩、又は10,000ppm未満の元素状ヨウ素を含む、請求項1に記載の方法。
- 前記レギオ選択性触媒が、一又は複数のヨードベンゼン又はハロゲン化ヨードベンゼン、フェニルクロロヨードニウムクロリド、ジアリールヨードニウム塩、ヨウ素化ポリマー、ヨードキシ化合物、ヨードソ化合物、モノ及び三ハロゲン化ヨウ素、ヨウ素酸化物、及び任意の数のこれらの誘導体又は組み合わせを含む非金属ヨウ化物を含んでなる、請求項3に記載の方法。
- 前記レギオ選択性触媒が、ヨウ素酸ナトリウム、過ヨウ素酸ナトリウム、又はこれらの組み合わせを含む無機ヨード塩を含んでなる、請求項3に記載の方法。
- 少なくとも二つの塩素化段階を前記レギオ選択性触媒で触媒する、請求項1に記載の方法。
- 一つの塩素化段階を塩化アルミニウムで触媒し、別の段階を非金属ヨウ化物、無機ヨード塩又は10,000ppm未満の元素状ヨウ素で触媒する、請求項6に記載の方法。
- 両段階を同じ反応器内で行う、請求項7に記載の方法。
- 少なくとも一つの塩素化段階を、フリーラジカル開始剤又はイオン性塩素化触媒の存在下で行い、前記フリーラジカル開始剤が、アゾビスイソブチロニトリル、1,1’−アゾビス(シクロヘキサンカルボニトリル)、ジ−tert−ブチルペルオキシド、過酸化ベンゾイル、過酸化ジベンゾイル、過酸化メチルエチルケトン、過酸化アセトン、又は任意の数のこれらの組み合わせを含む、請求項1に記載の方法。
- 少なくとも一つの脱塩化水素段階を更に含む、請求項1に記載の方法。
- 前記少なくとも一つの脱塩化水素段階を触媒の存在下で行う、請求項10に記載の方法。
- 塩素原子源が、塩化スルフリル、塩素又はこれらの組み合わせ、のいずれかを含む、請求項1に記載の方法。
- 前記方法を、更に、四塩化炭素及び/又は塩化スルフリルを含む溶媒の存在下で行う、請求項12に記載の方法。
- 前記一つのクロロプロパンが、1,1,2−トリクロロプロパン、1,1,2,2,3−ペンタクロロプロパン又はこれらの組み合わせを含むトリ−、又はペンタクロロプロパンである、請求項1に記載の方法。
- 前記塩素化プロペンが、1,1,2,3−テトラクロロプロペンを含む、請求項1に記載の方法。
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US201161570028P | 2011-12-13 | 2011-12-13 | |
US61/570,028 | 2011-12-13 | ||
US201261583799P | 2012-01-06 | 2012-01-06 | |
US61/583,799 | 2012-01-06 | ||
PCT/US2012/069230 WO2013090421A1 (en) | 2011-12-13 | 2012-12-12 | Process for the production of chlorinated propanes and propenes |
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JP6449791B2 (ja) | 2013-03-09 | 2019-01-09 | ブルー キューブ アイピー エルエルシー | クロロアルカンの製造方法 |
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- 2012-12-12 US US14/365,143 patent/US9334205B2/en not_active Expired - Fee Related
- 2012-12-12 CN CN201280061065.6A patent/CN104024188B/zh not_active Expired - Fee Related
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JP2017186364A (ja) * | 2011-05-31 | 2017-10-12 | ブルー キューブ アイピー エルエルシー | 塩素化プロペンの製造方法 |
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CN104024188B (zh) | 2018-05-01 |
JP6170068B2 (ja) | 2017-07-26 |
CN104024188A (zh) | 2014-09-03 |
US20140371494A1 (en) | 2014-12-18 |
US9334205B2 (en) | 2016-05-10 |
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