JP6629821B2 - 塩素化プロペンの製造方法 - Google Patents
塩素化プロペンの製造方法 Download PDFInfo
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- JP6629821B2 JP6629821B2 JP2017226599A JP2017226599A JP6629821B2 JP 6629821 B2 JP6629821 B2 JP 6629821B2 JP 2017226599 A JP2017226599 A JP 2017226599A JP 2017226599 A JP2017226599 A JP 2017226599A JP 6629821 B2 JP6629821 B2 JP 6629821B2
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- pentachloropropane
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- tetrachloropropane
- chlorination
- tetrachloropropene
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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
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
-
- 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
- C07C17/06—Preparation of halogenated hydrocarbons by addition of halogens combined with replacement of hydrogen atoms by halogens
-
- 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
-
- 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
-
- 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
-
- 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
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
[態様1]
1,2,3−トリクロロプロパンを含む供給流からの塩素化プロペンの製造方法であって、少なくとも1つの塩素化工程及び少なくとも1つの脱塩化水素化工程を含み、当該方法により生成した1,2,2,3−テトラクロロプロパンを再循環及び/又はさらに反応させる、塩素化プロペンの製造方法。
[態様2]
前記塩素化工程によりテトラクロロプロパンとペンタクロロプロパンとを含む混合物が生成する、上記態様1に記載の方法。
[態様3]
前記混合物が分離されて1,2,2,3−テトラクロロプロパンを含む流れをもたらす、上記態様2に記載の方法。
[態様4]
前記1,2,2,3−テトラクロロプロパン流れが第1塩素化工程に再循環される、上記態様3に記載の方法。
[態様5]
前記1,2,2,3−テトラクロロプロパン流れが第2塩素化工程において塩素化されて1,1,2,2,3−ペンタクロロプロパンをもたらす、上記態様3に記載の方法。
[態様6]
前記分離により、さらに、未反応の1,2,3−トリクロロプロパンの流れがもたらされ、当該未反応の1,2,3−トリクロロプロパンの流れは塩素化工程に再循環される、上記態様3に記載の方法。
[態様7]
前記分離により、さらに、HClの流れと未反応のCl 2 を含む流れがもたらされ、HClが当該方法から無水HClとして回収され、前記Cl 2 は再循環される、上記態様3に記載の方法。
[態様8]
前記分離により、さらに、1,1,2,3−テトラクロロプロパンを含む流れと、ペンタクロロプロパン異性体とより重質の副生成物とを含む流れがもたらされる、上記態様3に記載の方法。
[態様9]
1,1,2,3−テトラクロロプロパンを含む前記流れを脱塩化水素化してトリクロロプロペンを含む流れを生成させ、当該トリクロロプロペン流れを塩素化して1,1,1,2,3−ペンタクロロプロパンと1,1,2,2,3−ペンタクロロプロパンとを含む流れを生成させる、上記態様8に記載の方法。
[態様10]
前記少なくとも1つの塩素化工程が、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)、2,2’−アゾビス(2,4−ジメチルバレロニトリル)、ジメチル2,2’−アゾビス(2−メチルプロピオネート)又はこれらの組み合わせを含むフリーラジカル開始剤の存在下で行われる、上記態様1に記載の方法。
[態様11]
前記少なくとも1つの脱塩化水素化工程が、鉄、塩化第二鉄、塩化アルミニウム又はこれらの組み合わせを含む脱塩化水素化触媒の存在下で実施される、上記態様1に記載の方法。
[態様12]
前記混合物の残りを脱塩化水素化して、1,1,2,3−テトラクロロプロペン、2,3,3−テトラクロロプロパン、HCl及び未反応のペンタクロロプロパンを含む流れをもたらす、上記態様3に記載の方法。
[態様13]
前記未反応のペンタクロロプロパンを脱塩化水素化して1,1,2,3−テトラクロロプロペンを含む混合物をもたらす、上記態様12に記載の方法。
[態様14]
前記1,2,2,3−テトラクロロプロパンを脱塩化水素化工程に再循環させて1,2,3−トリクロロプロペンを生成させ、当該1,2,3−トリクロロプロペンを塩素化して1,1,2,2,3−ペンタクロロプロパンを生成させる、上記態様3に記載の方法。
[態様15]
上記態様1に記載の方法により製造した塩素化プロペンを2,3,3,3−テトラフルオロプロパ−1−エン又は1,3,3,3−テトラフルオロプロパ−1−エンに変換することを含む、2,3,3,3−テトラフルオロプロパ−1−エン又は1,3,3,3−テトラフルオロプロパ−1−エンの製造方法。
Claims (8)
- 1,1,2,3−テトラクロロプロペン及び2,3,3,3−テトラクロロプロペンの製造方法であって、
(a)1,2,3−トリクロロプロパンを含む供給流を第1塩素化工程にかけて1,2,3−トリクロロプロパン、1,2,2,3−テトラクロロプロパン、1,1,2,3−テトラクロロプロパン、1,1,2,2,3−ペンタクロロプロパン、1,1,1,2,3−ペンタクロロプロパン、1,1,2,3,3−ペンタクロロプロパン及びより重質の副生成物を含む生成物流を生成させる工程;
(b)工程(a)からの生成物流を分離して、
1,2,3−トリクロロプロパン及び任意に1,2,2,3−テトラクロロプロパンを含む流れと、
1,1,2,3−テトラクロロプロパンを含む流れと、
1,1,2,2,3−ペンタクロロプロパン、1,1,1,2,3−ペンタクロロプロパン、1,1,2,3,3−ペンタクロロプロパン及びより重質の副生成物を含む流れ、
を生成させる工程;
(c)工程(b)で生成した1,1,2,3−テトラクロロプロパンを含む流れを脱塩化水素化して少なくとも1種のトリクロロプロペンを含む流れを生成させる工程;
(d)工程(c)で生成した少なくとも1種のトリクロロプロペンを含む流れを第2塩素化工程にかけて1,1,1,2,3−ペンタクロロプロパン及び1,1,2,2,3−ペンタクロロプロパンを含む流れを生成させる工程;
(e)1,1,1,2,3−ペンタクロロプロパン及び1,1,2,2,3−ペンタクロロプロパンを含む工程(b)及び(d)からの生成物流を第2脱塩化水素化工程にかけて1,1,2,3−テトラクロロプロペン、2,3,3,3−テトラクロロプロペン、HCl、1,1,1,2,3−ペンタクロロプロパン及び1,1,2,2,3−ペンタクロロプロパンを生成させる工程であって、工程(b)及び/又は(d)からの生成物流の少なくとも一部が脱塩化水素化触媒の存在下で脱塩化水素化される工程;及び
(f)1,2,3−トリクロロプロパンを含む流れを第1塩素化工程に再循環させる工程、
を含み、
前記1,2,2,3−テトラクロロプロパンは第1塩素化工程に再循環されるか、もしくは前記1,2,2,3−テトラクロロプロパンは異なる塩素化反応器で塩素化されて1,1,2,2,3−ペンタクロロプロパンを形成するか、又は前記1,2,2,3−テトラクロロプロパンは脱塩化水素化され塩素化されて1,1,2,2,3−ペンタクロロプロパンを形成する、
1,1,2,3−テトラクロロプロペン及び2,3,3,3−テトラクロロプロペンの製造方法。 - さらに、1,2,2,3−テトラクロロプロパンと1,2,3−トリクロロプロパンを含む工程(b)からの生成物流を工程(a)に再循環させる工程を含む、請求項1に記載の方法。
- 工程(a)の第1塩素化が、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)、2,2’−アゾビス(2,4−ジメチルバレロニトリル)、ジメチル2,2’−アゾビス(2−メチルプロピオネート)又はこれらの組み合わせを含むフリーラジカル開始剤の存在下で行われ、及び/又は、少なくとも1つの脱塩化水素化工程が、鉄、塩化第二鉄、塩化アルミニウム又はこれらの組み合わせを含む脱塩化水素化触媒の存在下で実施される、請求項1又は2に記載の方法。
- さらに、(f)1,1,2,3−テトラクロロプロペン、2,3,3,3−テトラクロロプロペン、HCl、1,1,1,2,3−ペンタクロロプロパン及び1,1,2,2,3−ペンタクロロプロパンを含む工程(e)で生成した前記流れから1,1,2,3−テトラクロロプロペン及び2,3,3,3−テトラクロロプロペンを分離する工程を含む、請求項1〜3のいずれか一項に記載の方法。
- 工程(d)の第2塩素化が、少なくとも1種のイオン性塩素化触媒の存在下で実施される、請求項1〜4のいずれか一項に記載の方法。
- 前記少なくとも1種のイオン性塩素化触媒が、塩化アルミニウム、塩化第二鉄(FeCl3)及び他の鉄含有化合物、ヨウ素、硫黄、五塩化アンチモン(SbCl5)、三塩化ホウ素(BCl3)、ハロゲン化ランタン、金属トリフラート、又はそれらの組み合わせを含む、請求項5に記載の方法。
- さらに、フッ素化触媒の存在下で1,1,2,3−テトラクロロプロペンをフッ素化剤に接触させてヒドロフルオロオレフィンを生成させることを含む、請求項4〜6のいずれか一項に記載の方法。
- 前記ヒドロフルオロオレフィンが2,3,3,3−テトラフルオロプロパ−1−エン、1,3,3,3−テトラフルオロプロパ−1−エン、又はこれらの組み合わせを含む、請求項7に記載の方法。
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JP2016507590A (ja) | 2013-02-27 | 2016-03-10 | ブルー キューブ アイピー エルエルシー | 塩素化プロペンを生成するための方法 |
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EP2739596A1 (en) | 2014-06-11 |
JP6420145B2 (ja) | 2018-11-07 |
EP2739596B1 (en) | 2019-05-01 |
US20140163266A1 (en) | 2014-06-12 |
WO2013022676A1 (en) | 2013-02-14 |
US9475739B2 (en) | 2016-10-25 |
JP2018043992A (ja) | 2018-03-22 |
US20140163265A1 (en) | 2014-06-12 |
JP2014529588A (ja) | 2014-11-13 |
US8907148B2 (en) | 2014-12-09 |
CA2844319A1 (en) | 2013-02-14 |
CN108929192A (zh) | 2018-12-04 |
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