JP2017510543A - ネオペンチルグリコールの製造方法 - Google Patents
ネオペンチルグリコールの製造方法 Download PDFInfo
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- JP2017510543A JP2017510543A JP2016536163A JP2016536163A JP2017510543A JP 2017510543 A JP2017510543 A JP 2017510543A JP 2016536163 A JP2016536163 A JP 2016536163A JP 2016536163 A JP2016536163 A JP 2016536163A JP 2017510543 A JP2017510543 A JP 2017510543A
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- Prior art keywords
- isobutyraldehyde
- neopentyl glycol
- formaldehyde
- catalyst
- basic catalyst
- Prior art date
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
- C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/85—Chromium, molybdenum or tungsten
- B01J23/86—Chromium
- B01J23/862—Iron and chromium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/85—Chromium, molybdenum or tungsten
- B01J23/86—Chromium
- B01J23/866—Nickel and chromium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/85—Chromium, molybdenum or tungsten
- B01J23/86—Chromium
- B01J23/868—Chromium copper and chromium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/889—Manganese, technetium or rhenium
- B01J23/8892—Manganese
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0237—Amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
- C07C29/84—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation by extractive distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/94—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/20—Dihydroxylic alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/75—Reactions with formaldehyde
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
- C07C47/19—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing hydroxy groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
a)塩基性触媒の存在下に、イソブチルアルデヒドをホルムアルデヒドと反応させる工程であって、その際、該イソブチルアルデヒドが過剰に存在する、工程
b)工程a)からの反応混合物を蒸留による精製によって底部生成物を生じさせる工程であって、該底部生成物は、≦5重量%の水を含有する、工程、
c)該底部生成物を水素化してネオペンチルグリコールにする工程。
この反応は、好ましくは、≧40℃〜≦100℃の温度で行われ、連続的又は断続的に行うことができる。
工程b)は、好ましくは、薄膜蒸留器で行われる。これは、好ましくは、10個〜30個の底部に搭載されたカラムを介して行われる。さらに好ましくは、≧170℃〜≦200℃の温度である。
好ましくは、工程c)は、工程b)の直後に行われ、これはすなわち、本発明の好ましい実施形態によれば、工程b)と工程c)の間には蒸留生成物のさらなる精製が存在しない。
2.8kgの硝酸銅三水和物、400gの硝酸マンガン(希硝酸中の50%濃度溶液)及び150gの硝酸バリウムを、20Lの蒸留H2O中に55℃で溶解する。別途、2.6kgの重クロム酸アンモニウムを12Lの水及び4Lの25%濃度アンモニア溶液中に溶解する。
47.5%銅、46.5%クロム、4.0%マンガン、2.0%バリウム
3996gのイソブチルアルデヒド(97.4%濃度)及び3034gのホルマリン(49%濃度の水溶液)を、オートクレーブに仕込み、そして、45℃に加熱する。引き続いて、151gのトリメチルアミン(40%濃度の水溶液)を汲み入れる(zugepumpt)。添加後すぐに、反応混合物を90℃に加熱し、そして、1時間その温度で放置する。引き続いて、生成物を排出させる。生成物の組成は次のとおりである。
加熱速度:20℃/時間、180℃まで
窒素:1000NL/時間
水素: 20NL/時間
期間:12時間
窒素:1000NL/時間
水素: 60NL/時間
期間:6時間
窒素:1000NL/時間
水素: 120NL/時間
期間:6時間
Claims (10)
- a)塩基性触媒の存在下に、イソブチルアルデヒドをホルムアルデヒドと反応させる工程であって、その際、該イソブチルアルデヒドが過剰に存在する、工程
b)工程a)からの反応混合物を蒸留による精製によって底部生成物を生じさせる工程であって、該底部生成物が、5重量%未満の水を含有する、工程、
c)該底部生成物を水素化してネオペンチルグリコールにする工程、
を含む、ネオペンチルグリコールの合成方法。 - 前記イソブチルアルデヒドのホルムアルデヒドに対する比が≧1.01:1(イソブチルアルデヒドのモルのホルムアルデヒドのモルに対する)である、請求項1に記載の方法。
- 前記塩基性触媒が、前記イソブチルアルデヒドに対して、好ましくは≧0.01〜≦0.1のモル比で使用される、請求項1又は2に記載の方法。
- 前記塩基性触媒が、トリメチルアミン及び/又は苛性ソーダを含む、請求項1〜3のいずれか一つに記載の方法。
- 工程b)が、薄膜蒸発器において遂行される、請求項1〜4のいずれか一つに記載の方法。
- 工程b)が遂行された後に、下記の工程b1):
b1)工程b)で分離された、イソブチルアルデヒドを含有する有機相を、工程a)による新たな反応にフィードバックする工程、
を追加的に含む、請求項1〜5のいずれか一つに記載の方法。 - 工程b)と工程c)との間に、前記蒸留排液の更なる精製が行われない、請求項1〜6のいずれか一つに記載の方法。
- 工程c)が、≧6MPa〜≦20MPaの水素の圧力で行われる、請求項1〜7のいずれか一つに記載の方法。
- 工程c)が、二段階又は多段階の水素化として、マルチゾーンリアクター中で遂行される、請求項1〜8のいずれか一つに記載の方法。
- 工程c)が、ニッケル及び/又は銅クロマイトをベースとする触媒を含む、請求項1〜9のいずれか一つに記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102014100996.7 | 2014-01-28 | ||
DE102014100996.7A DE102014100996B4 (de) | 2014-01-28 | 2014-01-28 | Verfahren zur Herstellung von Neopentylglykol |
PCT/EP2015/051466 WO2015113928A1 (de) | 2014-01-28 | 2015-01-26 | Verfahren zur herstellung von neopentylglykol |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2017510543A true JP2017510543A (ja) | 2017-04-13 |
JP2017510543A5 JP2017510543A5 (ja) | 2018-02-01 |
JP6373385B2 JP6373385B2 (ja) | 2018-08-15 |
Family
ID=52598713
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2016536163A Active JP6373385B2 (ja) | 2014-01-28 | 2015-01-26 | ネオペンチルグリコールの製造方法 |
Country Status (7)
Country | Link |
---|---|
US (1) | US20160326073A1 (ja) |
EP (1) | EP3099656B1 (ja) |
JP (1) | JP6373385B2 (ja) |
KR (1) | KR101846755B1 (ja) |
CN (1) | CN105764879B (ja) |
DE (1) | DE102014100996B4 (ja) |
WO (1) | WO2015113928A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2023502620A (ja) * | 2020-10-16 | 2023-01-25 | エルジー・ケム・リミテッド | ネオペンチルグリコールの製造方法 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3747855B1 (de) * | 2019-06-04 | 2024-01-10 | OQ Chemicals GmbH | Verfahren zur kontinuierlichen herstellung von diolen aus aldehyden mittels raney-cobalt katalyse |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5118928A (ja) * | 1974-08-08 | 1976-02-14 | Aikoh Co | Uwatsugizokaiyoyumenhifukuban |
JPS554396A (en) * | 1978-06-24 | 1980-01-12 | Huels Chemische Werke Ag | Manufacture of pure neopentylglycol |
JP2002500208A (ja) * | 1997-12-30 | 2002-01-08 | ネステ ケミカルズ オサケ ユキテュア | ネオペンチルグリコールの調製プロセス |
DE10317545A1 (de) * | 2003-04-16 | 2004-11-04 | Basf Ag | Verfahren zur Herstellung von Neopentylglykol und Hydroxypivalinsäureneopentylglykolester |
JP2008506775A (ja) * | 2004-07-19 | 2008-03-06 | ジーアールティー,インコーポレイティド | ゾーンリアクター |
JP2010520250A (ja) * | 2007-03-02 | 2010-06-10 | ビーエーエスエフ ソシエタス・ヨーロピア | ヒドロキシピバリンアルデヒドおよびネオペンチルグリコールの製造法 |
JP2012511534A (ja) * | 2008-12-09 | 2012-05-24 | ビーエーエスエフ ソシエタス・ヨーロピア | ポリメチロールの製造方法 |
JP2013237046A (ja) * | 2008-02-11 | 2013-11-28 | Catalytic Distillation Technologies | 有機カーボネート又は有機カルバメートを連続生産するための製造方法、及び、そのための固体触媒 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102008031338B4 (de) * | 2008-07-02 | 2012-09-13 | Oxea Gmbh | Verfahren zur Herstellung von Neopentylglykol |
TW201247618A (en) * | 2011-04-19 | 2012-12-01 | Basf Se | Process for preparing neopentyl glycol |
WO2012143309A1 (de) * | 2011-04-19 | 2012-10-26 | Basf Se | Verfahren zur herstellung von neopentylglykol |
CN102391068A (zh) * | 2011-07-29 | 2012-03-28 | 淇县彤邦化工有限公司 | 一种蒸馏水连续运行新工艺 |
-
2014
- 2014-01-28 DE DE102014100996.7A patent/DE102014100996B4/de active Active
-
2015
- 2015-01-26 KR KR1020167011714A patent/KR101846755B1/ko active IP Right Grant
- 2015-01-26 WO PCT/EP2015/051466 patent/WO2015113928A1/de active Application Filing
- 2015-01-26 US US15/037,346 patent/US20160326073A1/en not_active Abandoned
- 2015-01-26 JP JP2016536163A patent/JP6373385B2/ja active Active
- 2015-01-26 EP EP15707553.2A patent/EP3099656B1/de active Active
- 2015-01-26 CN CN201580002718.7A patent/CN105764879B/zh active Active
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5118928A (ja) * | 1974-08-08 | 1976-02-14 | Aikoh Co | Uwatsugizokaiyoyumenhifukuban |
JPS554396A (en) * | 1978-06-24 | 1980-01-12 | Huels Chemische Werke Ag | Manufacture of pure neopentylglycol |
JP2002500208A (ja) * | 1997-12-30 | 2002-01-08 | ネステ ケミカルズ オサケ ユキテュア | ネオペンチルグリコールの調製プロセス |
DE10317545A1 (de) * | 2003-04-16 | 2004-11-04 | Basf Ag | Verfahren zur Herstellung von Neopentylglykol und Hydroxypivalinsäureneopentylglykolester |
JP2008506775A (ja) * | 2004-07-19 | 2008-03-06 | ジーアールティー,インコーポレイティド | ゾーンリアクター |
JP2010520250A (ja) * | 2007-03-02 | 2010-06-10 | ビーエーエスエフ ソシエタス・ヨーロピア | ヒドロキシピバリンアルデヒドおよびネオペンチルグリコールの製造法 |
JP2013237046A (ja) * | 2008-02-11 | 2013-11-28 | Catalytic Distillation Technologies | 有機カーボネート又は有機カルバメートを連続生産するための製造方法、及び、そのための固体触媒 |
JP2012511534A (ja) * | 2008-12-09 | 2012-05-24 | ビーエーエスエフ ソシエタス・ヨーロピア | ポリメチロールの製造方法 |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2023502620A (ja) * | 2020-10-16 | 2023-01-25 | エルジー・ケム・リミテッド | ネオペンチルグリコールの製造方法 |
JP7419646B2 (ja) | 2020-10-16 | 2024-01-23 | エルジー・ケム・リミテッド | ネオペンチルグリコールの製造方法 |
Also Published As
Publication number | Publication date |
---|---|
DE102014100996A1 (de) | 2015-07-30 |
CN105764879A (zh) | 2016-07-13 |
KR20160114040A (ko) | 2016-10-04 |
JP6373385B2 (ja) | 2018-08-15 |
CN105764879B (zh) | 2017-09-08 |
KR101846755B1 (ko) | 2018-05-18 |
EP3099656A1 (de) | 2016-12-07 |
US20160326073A1 (en) | 2016-11-10 |
WO2015113928A1 (de) | 2015-08-06 |
EP3099656B1 (de) | 2018-03-14 |
DE102014100996B4 (de) | 2018-11-15 |
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