JP2009501203A - プロセス - Google Patents
プロセス Download PDFInfo
- Publication number
- JP2009501203A JP2009501203A JP2008520964A JP2008520964A JP2009501203A JP 2009501203 A JP2009501203 A JP 2009501203A JP 2008520964 A JP2008520964 A JP 2008520964A JP 2008520964 A JP2008520964 A JP 2008520964A JP 2009501203 A JP2009501203 A JP 2009501203A
- Authority
- JP
- Japan
- Prior art keywords
- glycerin
- catalyst
- hydrogen
- process according
- bar
- 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.)
- Granted
Links
Classifications
-
- 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
-
- 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
- C07C29/60—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by elimination of -OH groups, e.g. by dehydration
-
- 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
- C07C31/02—Monohydroxylic acyclic alcohols
- C07C31/10—Monohydroxylic acyclic alcohols containing three carbon atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
0.75インチの反応器にデイビー プロセス テクノロジー リミテッド製の銅含有触媒である触媒DRD9289Aを75g(50ml)充填し、従来の方法によって還元した。グリセリンとメタノールの供給原料を反応圧力で水素と共に加熱した容器に送り、供給原料混合物を完全に気化した。次に、得られた気体流を反応器に送り、触媒と接触させた。反応器から取り出した生成物は10℃で凝縮し、マイクロTCD検出器を備えたHewlett Packard HP3560 GCで分析した。それぞれの実施例の条件を表1に示し、その結果を表2に示す。
Claims (16)
- グリセリンの水素添加方法であって、
気相中、触媒の存在下、温度が約160℃から約260℃、圧力が約10から約30バール、水素とグリセリンの比率が400:1から約600:1、滞留時間が約0.01から約2.5hr−1で、グリセリンを含む供給原料を水素含有気流と接触させて、水素添加させる方法。 - グリセリン供給原料は、水素添加反応器に送られる前に、気化器中で水素含有気流中に気化させる請求項1記載の方法。
- 前記触媒が、水素添加反応器中に配置された固定床として設けられている請求項1または2記載の方法。
- 前記触媒が還元銅触媒である請求項1〜3のいずれかに記載の方法。
- 反応温度が約200℃から約240℃である請求項1〜4のいずれかに記載の方法。
- 反応温度が約205℃から約220℃である請求項1〜5のいずれかに記載の方法。
- 反応圧力が約17バールから約23バールである請求項1〜6のいずれかに記載の方法。
- 反応圧力が約20バール以上である請求項1〜7のいずれかに記載の方法。
- 滞留時間が約0.3秒から約1.5秒である請求項1〜8のいずれかに記載の方法。
- 滞留時間が約0.5秒である請求項1〜8のいずれかに記載の方法。
- 水素とグリセリンの比率が約450:1から約550:1である請求項1〜10のいずれかに記載の方法。
- 水素とグリセリンの比率が約500:1以上である請求項1〜11のいずれかに記載の方法。
- この方法が1,2−プロパンジオールの生成に選択的である請求項1〜12のいずれかに記載の方法。
- 温度が約210℃未満である請求項13記載の方法。
- この方法がプロパノールの生成に選択的である請求項1〜12のいずれかに記載の方法。
- 温度が約210℃以上である請求項15記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB0514593.3 | 2005-07-15 | ||
GBGB0514593.3A GB0514593D0 (en) | 2005-07-15 | 2005-07-15 | Process |
PCT/GB2006/050181 WO2007010299A1 (en) | 2005-07-15 | 2006-06-30 | Process |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2009501203A true JP2009501203A (ja) | 2009-01-15 |
JP2009501203A5 JP2009501203A5 (ja) | 2009-07-16 |
JP5149796B2 JP5149796B2 (ja) | 2013-02-20 |
Family
ID=34897311
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2008520964A Expired - Fee Related JP5149796B2 (ja) | 2005-07-15 | 2006-06-30 | プロセス |
Country Status (19)
Country | Link |
---|---|
US (1) | US7355083B2 (ja) |
EP (1) | EP1836147B1 (ja) |
JP (1) | JP5149796B2 (ja) |
KR (1) | KR101325084B1 (ja) |
CN (1) | CN101006036B (ja) |
AR (1) | AR058013A1 (ja) |
AU (1) | AU2006252177B2 (ja) |
BR (1) | BRPI0606159B1 (ja) |
CA (1) | CA2569622C (ja) |
DK (1) | DK1836147T3 (ja) |
EA (1) | EA010314B1 (ja) |
ES (1) | ES2298101T3 (ja) |
GB (1) | GB0514593D0 (ja) |
MY (1) | MY142306A (ja) |
NZ (1) | NZ551994A (ja) |
PL (1) | PL1836147T3 (ja) |
TW (1) | TWI394740B (ja) |
WO (1) | WO2007010299A1 (ja) |
ZA (1) | ZA200700897B (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2009179594A (ja) * | 2008-01-30 | 2009-08-13 | Kao Corp | 多価アルコールの水素化分解物の製造方法 |
KR20140010437A (ko) * | 2011-03-10 | 2014-01-24 | 쥐티씨 테크놀로지 유에스,엘엘씨 | 글리세린을 프로필렌 글리콜로 변환시키는 방법 |
Families Citing this family (41)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101346302B (zh) * | 2005-12-21 | 2013-07-10 | 维仁特公司 | 用于重整含氧化合物的催化剂及方法 |
PL2565176T3 (pl) * | 2006-05-08 | 2016-01-29 | Virent Inc | Sposoby wytwarzania polio li |
US7619118B2 (en) | 2006-06-07 | 2009-11-17 | The Procter & Gamble Company | Process for the conversion of glycerol to propylene glycol and amino alcohols |
US7619119B2 (en) | 2006-06-07 | 2009-11-17 | The Procter & Gamble Company | Processes for converting glycerol to amino alcohols |
GB0614823D0 (en) | 2006-07-26 | 2006-09-06 | Davy Process Techn Ltd | Process |
DE102006050751A1 (de) | 2006-10-27 | 2008-05-08 | Clariant International Limited | Verfahren zur Herstellung von 1,2-Propandiol durch Hydrogenolyse von Glycerin |
US20100288975A1 (en) * | 2006-12-20 | 2010-11-18 | Cortright Randy D | Reactor system for producing gaseous products |
DE102007003188B3 (de) | 2007-01-22 | 2008-06-05 | Clariant International Ltd. | Verfahren zur Herstellung von 1,2-Propandiol durch Hydrogenolyse von Glycerin |
ES2817876T3 (es) | 2007-03-08 | 2021-04-08 | Virent Inc | Síntesis de combustibles líquidos a partir de hidrocarburos oxigenados |
BRPI0701993A2 (pt) * | 2007-03-30 | 2008-11-18 | Petroleo Brasileiro Sa | mÉtodo para reciclagem e aproveitamento da glicerina obtida da produÇço do biodiesel |
EP2138478B1 (en) | 2007-04-17 | 2019-07-24 | Kao Corporation | Process for producing hydrogenolysis products of polyhydric alcohols |
JP5302543B2 (ja) * | 2008-01-21 | 2013-10-02 | 花王株式会社 | 多価アルコールの水素化分解物の製造方法 |
EP2162416B8 (en) * | 2007-05-18 | 2018-12-19 | BioFuel-Solution i Malmö AB | Gas phase process for monoalcohol production from glycerol |
KR100870369B1 (ko) * | 2007-08-29 | 2008-11-25 | 지에스칼텍스 주식회사 | 프로판디올 제조용 촉매의 제조 방법 및 이를 이용한프로판디올의 제조 방법 |
WO2009027502A2 (de) * | 2007-08-31 | 2009-03-05 | Basf Se | Verfahren zur herstellung von 1,2-propandiol durch niederdruck-hydrierung von glycerin |
BRPI0815783A2 (pt) * | 2007-08-31 | 2015-02-24 | Basf Se | Processo para a preparação de 1,2-propanodiol. |
WO2009027500A2 (de) * | 2007-08-31 | 2009-03-05 | Basf Se | Verfahren zur herstellung von 1,2-propandiol durch hydrierung von glycerin in einer zweistufigen reaktorkaskade |
US8053608B2 (en) * | 2007-10-31 | 2011-11-08 | Mitsui Chemicals, Inc. | Process for producing propylene glycol |
GB0724232D0 (en) | 2007-12-12 | 2008-01-23 | Davy Process Techn Ltd | Process |
CN101456791B (zh) | 2007-12-13 | 2012-07-04 | 中国科学院兰州化学物理研究所 | 利用生物基甘油生产1,2-丙二醇的方法 |
JP5305669B2 (ja) * | 2008-01-21 | 2013-10-02 | 花王株式会社 | 多価アルコールの水素化分解物の製造方法 |
AR072446A1 (es) * | 2008-03-02 | 2010-09-01 | Dow Global Technologies Inc | Proceso de hidrogenacion mejorado |
US20090246430A1 (en) | 2008-03-28 | 2009-10-01 | The Coca-Cola Company | Bio-based polyethylene terephthalate polymer and method of making same |
US8378152B2 (en) * | 2008-04-30 | 2013-02-19 | Mitsui Chemicals, Inc. | Method of producing propylene glycol |
DE102008027601A1 (de) | 2008-06-10 | 2009-12-17 | Clariant International Limited | Verfahren zur Herstellung von 1,2-Propandiol durch Hydrogenolyse von Glycerin |
BRPI0803898A2 (pt) * | 2008-07-30 | 2010-11-09 | Univ Rio De Janeiro | processo catalìtico para a transformação de glicerina em insumos para o setor petroquìmico |
JP5555867B2 (ja) * | 2008-08-04 | 2014-07-23 | 国立大学法人 千葉大学 | グリセリンからのグリコール及び1−プロパノールの製造方法 |
WO2010025241A2 (en) * | 2008-08-27 | 2010-03-04 | Virent Energy Systems, Inc. | Synthesis of liquid fuels from biomass |
US8071820B2 (en) * | 2008-12-23 | 2011-12-06 | Uop Llc | Method for converting glycerol to propanol |
KR101050058B1 (ko) * | 2008-12-31 | 2011-07-19 | 서울대학교산학협력단 | 프로판디올 제조용 촉매의 제조 방법 및 그를 이용한 프로판디올의 제조 방법 |
US20100189791A1 (en) | 2009-01-23 | 2010-07-29 | Teva Pharmaceutical Industries, Ltd. | Delayed release rasagiline malate formulation |
SG173818A1 (en) | 2009-02-25 | 2011-09-29 | Grace W R & Co | Process for making 1, 2-propane diol from hydrogenation of glycerol |
AU2010221723A1 (en) | 2009-03-03 | 2011-09-22 | The Coca-Cola Company | Bio-based polyethylene terephthalate packaging and method of making thereof |
WO2010150278A2 (en) | 2009-06-15 | 2010-12-29 | Ganapati Dadasaheb Yadav; | Hydrogenolysis of polyhydroxy alcohols using metal incorporated manganese oxide octahedral molecular sieve as a catalyst |
WO2011002912A2 (en) * | 2009-06-30 | 2011-01-06 | Virent Energy Systems, Inc. | Process and reactor systems for converting sugars and sugar alcohols |
WO2011009936A2 (en) | 2009-07-24 | 2011-01-27 | Basf Se | Process for the preparation of 1,2-propanediol from glycerol |
BRPI1000430A2 (pt) | 2010-02-24 | 2011-10-25 | Petroleo Brasileiro Sa | produção de propilenoglicol a partir de glicerina |
DE102010015006A1 (de) | 2010-04-14 | 2011-11-24 | Tu Darmstadt | Katalysator zur Hydrierung von wässrigen mehrwertigen Alkohollösungen |
CN102924233B (zh) * | 2012-10-20 | 2015-04-15 | 青岛科技大学 | 一种甘油氢解制备丙二醇的方法 |
AR095195A1 (es) | 2013-03-15 | 2015-09-30 | W R Grace & Co -Conn | Proceso para la producción selectiva de propanoles por hidrogenación de glicerol |
CN107673952A (zh) * | 2017-09-26 | 2018-02-09 | 龙岩卓越生物基材料有限公司 | 利用生物甘油制备1,2‑丙二醇及正丙醇的方法 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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DE524101C (de) * | 1926-01-13 | 1931-05-11 | I G Farbenindustrie Akt Ges | Verfahren zur UEberfuehrung von hoeherwertigen Alkoholen in niedrigerwertige |
DE4302464A1 (de) * | 1993-01-29 | 1994-08-04 | Henkel Kgaa | Herstellung von 1,2-Propandiol aus Glycerin |
JP2001510816A (ja) * | 1997-07-23 | 2001-08-07 | シエル・インターナシヨナル・リサーチ・マートスハツペイ・ベー・ヴエー | グリセロールの水素化分解 |
JP2003261550A (ja) * | 2002-03-06 | 2003-09-19 | Sumitomo Chem Co Ltd | プロピレンオキサイド及びプロピルアルコールの製造方法 |
JP2004501126A (ja) * | 2000-06-20 | 2004-01-15 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ジオールおよびポリオールの触媒脱ヒドロキシル化 |
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BR8204165A (pt) | 1981-07-22 | 1983-07-12 | Du Pont | Processo para hidrogenolise de pentitois e misturas de pentitois com outros glicois hexitois e misturas de hexitois com outros poliois e poliois para etileno glicol |
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US6841085B2 (en) * | 2001-10-23 | 2005-01-11 | Battelle Memorial Institute | Hydrogenolysis of 6-carbon sugars and other organic compounds |
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-
2005
- 2005-07-15 GB GBGB0514593.3A patent/GB0514593D0/en not_active Ceased
-
2006
- 2006-06-30 KR KR1020077000311A patent/KR101325084B1/ko not_active IP Right Cessation
- 2006-06-30 ES ES06744361T patent/ES2298101T3/es active Active
- 2006-06-30 PL PL06744361T patent/PL1836147T3/pl unknown
- 2006-06-30 EP EP06744361A patent/EP1836147B1/en active Active
- 2006-06-30 CN CN2006800006177A patent/CN101006036B/zh not_active Expired - Fee Related
- 2006-06-30 WO PCT/GB2006/050181 patent/WO2007010299A1/en not_active Application Discontinuation
- 2006-06-30 DK DK06744361.4T patent/DK1836147T3/da active
- 2006-06-30 CA CA2569622A patent/CA2569622C/en not_active Expired - Fee Related
- 2006-06-30 ZA ZA200700897A patent/ZA200700897B/en unknown
- 2006-06-30 BR BRPI0606159-1A patent/BRPI0606159B1/pt not_active IP Right Cessation
- 2006-06-30 EA EA200700445A patent/EA010314B1/ru not_active IP Right Cessation
- 2006-06-30 JP JP2008520964A patent/JP5149796B2/ja not_active Expired - Fee Related
- 2006-06-30 AU AU2006252177A patent/AU2006252177B2/en not_active Ceased
- 2006-06-30 NZ NZ551994A patent/NZ551994A/en not_active IP Right Cessation
- 2006-07-07 MY MYPI20063248A patent/MY142306A/en unknown
- 2006-07-13 AR ARP060103005A patent/AR058013A1/es not_active Application Discontinuation
- 2006-07-14 TW TW095125853A patent/TWI394740B/zh not_active IP Right Cessation
-
2007
- 2007-01-30 US US11/668,884 patent/US7355083B2/en not_active Expired - Fee Related
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE524101C (de) * | 1926-01-13 | 1931-05-11 | I G Farbenindustrie Akt Ges | Verfahren zur UEberfuehrung von hoeherwertigen Alkoholen in niedrigerwertige |
DE4302464A1 (de) * | 1993-01-29 | 1994-08-04 | Henkel Kgaa | Herstellung von 1,2-Propandiol aus Glycerin |
JP2001510816A (ja) * | 1997-07-23 | 2001-08-07 | シエル・インターナシヨナル・リサーチ・マートスハツペイ・ベー・ヴエー | グリセロールの水素化分解 |
JP2004501126A (ja) * | 2000-06-20 | 2004-01-15 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ジオールおよびポリオールの触媒脱ヒドロキシル化 |
JP2003261550A (ja) * | 2002-03-06 | 2003-09-19 | Sumitomo Chem Co Ltd | プロピレンオキサイド及びプロピルアルコールの製造方法 |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2009179594A (ja) * | 2008-01-30 | 2009-08-13 | Kao Corp | 多価アルコールの水素化分解物の製造方法 |
KR20140010437A (ko) * | 2011-03-10 | 2014-01-24 | 쥐티씨 테크놀로지 유에스,엘엘씨 | 글리세린을 프로필렌 글리콜로 변환시키는 방법 |
JP2014514276A (ja) * | 2011-03-10 | 2014-06-19 | ジーティーシー テクノロジー ユーエス, エルエルシー | グリセリンをプロピレングリコールに転換する方法 |
KR101878852B1 (ko) * | 2011-03-10 | 2018-07-16 | 쥐티씨 테크놀로지 유에스,엘엘씨 | 글리세린을 프로필렌 글리콜로 변환시키는 방법 |
Also Published As
Publication number | Publication date |
---|---|
TWI394740B (zh) | 2013-05-01 |
KR20080025357A (ko) | 2008-03-20 |
ZA200700897B (en) | 2008-07-30 |
CA2569622C (en) | 2013-08-27 |
JP5149796B2 (ja) | 2013-02-20 |
EA200700445A1 (ru) | 2007-06-29 |
AU2006252177A2 (en) | 2008-08-07 |
GB0514593D0 (en) | 2005-08-24 |
MY142306A (en) | 2010-11-15 |
EA010314B1 (ru) | 2008-08-29 |
ES2298101T3 (es) | 2013-04-17 |
ES2298101T1 (es) | 2008-05-16 |
BRPI0606159B1 (pt) | 2015-08-11 |
WO2007010299A1 (en) | 2007-01-25 |
US20070149830A1 (en) | 2007-06-28 |
CN101006036A (zh) | 2007-07-25 |
EP1836147A1 (en) | 2007-09-26 |
AR058013A1 (es) | 2008-01-23 |
PL1836147T3 (pl) | 2013-06-28 |
BRPI0606159A2 (pt) | 2009-06-13 |
AU2006252177A1 (en) | 2007-02-01 |
AU2006252177B2 (en) | 2011-06-23 |
CA2569622A1 (en) | 2007-01-15 |
NZ551994A (en) | 2010-05-28 |
CN101006036B (zh) | 2011-09-07 |
DK1836147T3 (da) | 2013-04-22 |
KR101325084B1 (ko) | 2013-11-06 |
US7355083B2 (en) | 2008-04-08 |
TW200708500A (en) | 2007-03-01 |
EP1836147B1 (en) | 2013-02-20 |
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