KR940002207A - 1,3-프로판디올의 제조방법 - Google Patents

1,3-프로판디올의 제조방법 Download PDF

Info

Publication number
KR940002207A
KR940002207A KR1019930012797A KR930012797A KR940002207A KR 940002207 A KR940002207 A KR 940002207A KR 1019930012797 A KR1019930012797 A KR 1019930012797A KR 930012797 A KR930012797 A KR 930012797A KR 940002207 A KR940002207 A KR 940002207A
Authority
KR
South Korea
Prior art keywords
propanediol
reaction mixture
solid catalyst
acid
process according
Prior art date
Application number
KR1019930012797A
Other languages
English (en)
Other versions
KR100276538B1 (ko
Inventor
하스 토마스
아른츠 디트리히
Original Assignee
볼프강 메르크, 볼프강 베버
데구사 아크티엔게젤샤프트
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by 볼프강 메르크, 볼프강 베버, 데구사 아크티엔게젤샤프트 filed Critical 볼프강 메르크, 볼프강 베버
Publication of KR940002207A publication Critical patent/KR940002207A/ko
Application granted granted Critical
Publication of KR100276538B1 publication Critical patent/KR100276538B1/ko

Links

Classifications

    • 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
    • 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
    • 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
    • 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
    • C07C45/64—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 introduction of functional groups containing oxygen only in singly bound form

Abstract

1,3-프로판디올(PD)은 아크롤레인을 3-하이드록시 프로피온알데히드(HPA)로 수화시킨 다음, 촉매에 의해 수소화시킴으로써 수득된다. 수율을 감소시키는 부산물로서 4-옥사-1,7-헵탄디올(OD)이 생성된다.
본 발명에 따라, 1,3-프로판디올의 수율을 증가시키기 위해, PD와 OD를 함유하는 반응 혼합물을 후처리 하는 동안 증류에 의해 분리된 수용액 사아태에서 OD를 100 내지 300℃에서 산 고체 촉매, 특히 산 제올라이트를 사용하여 처리한 다음, 고체 촉매가 제거된 반응 혼합물을 PD와 OD를 함유하는 반응 혼합물의 후처리 단계로 환원시킨다.

Description

1,3-프로판디올의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (6)

  1. (a)아크롤레인을 산 수화촉매의 존재하에 수화시키는 단계, (b) 미반응 아크롤레인이 제거되었으며 3-하이드록시 프로피온알데히드를 함유하는 단계(a)의 반응 혼합물을 촉매에 의해 수소화시키는 단계 및 (c) 물, 1,3-프로판 디올 및 비점이 1,3-프로판디올 보다 높은 부산물을 함유하는 단계(b)의 반응 혼합물을 증류시켜 후처리하는 단계를 포함하여 1,3-프로판디올을 제조함에 있어서, 비점이 1,3-프로판디올보다 높은 부산물을 증류시켜 이로부터 4-옥사-1,7-헵탄디올을 분리하고, 100 내지 300℃에서 수용액 상태에서 산 고체 촉매로 처리하여 에테르 절단시킨 다음, 고체 촉매가 제거된 반응 혼합물을 단계(c)로 환원시킴을 특징으로 하는 방법.
  2. 제1항에 있어서, 4-옥사-1,7-헵탄디올이 5 내지 40 중량%, 바람직하게는 10 내지 30 중량%의 수용액상태로 에테르 절단단계에 공급됨을 특징으로 하는 방법.
  3. 제1항 또는 제2항에 있어서, 산 제올라이트, 바람직하게는 Si/Al의 원자비가 2 내지 약 100 이상, 특히 10 내지 약 40 이상인 산 제올라이트가 에테르 절단용 산 고체 촉매로서 사용됨을 특징으로 하는 방법.
  4. 제3항에 있어서, ZSM5형 제올라이트가 사용됨을 특징으로 하는 방법.
  5. 제1항 내지 제4항 중의 어느 한 항에 있어서, 에테르가 150 내지 250℃에서 절단됨을 특징으로 하는 방법.
  6. 제1항 내지 제5항 중의 어느 한 항에 있어서, 고정상 반응기에 배치된 산 고체 촉매상에 4-옥사-1,7-헵탄디올 수용액을 공급함으로써 에테르가 연속적으로 절단됨을 특징으로 하는 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019930012797A 1992-07-10 1993-07-08 1,3-프로판디올의 제조방법 KR100276538B1 (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4222708A DE4222708A1 (de) 1992-07-10 1992-07-10 Verfahren zur Herstellung von 1,3-Propandiol
DEP4222708.9 1992-07-10

Publications (2)

Publication Number Publication Date
KR940002207A true KR940002207A (ko) 1994-02-16
KR100276538B1 KR100276538B1 (ko) 2000-12-15

Family

ID=6462928

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019930012797A KR100276538B1 (ko) 1992-07-10 1993-07-08 1,3-프로판디올의 제조방법

Country Status (8)

Country Link
US (1) US5364987A (ko)
EP (1) EP0577972B1 (ko)
JP (1) JP3380295B2 (ko)
KR (1) KR100276538B1 (ko)
AT (1) ATE133402T1 (ko)
CA (1) CA2100229C (ko)
DE (2) DE4222708A1 (ko)
TW (1) TW277056B (ko)

Families Citing this family (64)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5463146A (en) * 1994-09-30 1995-10-31 Shell Oil Company Process for preparing 1,3-propanediol
US5545767A (en) * 1994-09-30 1996-08-13 Shell Oil Company Process for preparing 1,3-propanediol
US5463145A (en) * 1994-09-30 1995-10-31 Shell Oil Company Process for preparing 1,3-propanediol
US5463144A (en) * 1994-09-30 1995-10-31 Shell Oil Company Process for preparing 1,3-propanediol
US6187963B1 (en) * 1997-03-27 2001-02-13 Union Carbide Chemicals & Plastics Technology Corporation Processes for the manufacture of acrolein derivatives
US6235948B1 (en) 1998-08-18 2001-05-22 E. I. Du Pont De Nemours And Company Process for the purification of 1,3-propanediol
DE19926165C2 (de) 1999-06-09 2001-06-21 Degussa Verfahren zur Herstellung von 1,3-Dichlorpropan
US6284930B1 (en) 1999-07-30 2001-09-04 E.I. Du Pont De Nemours And Company Process for the preparation of 3-hydroxypropanal
US6342646B1 (en) 1999-07-30 2002-01-29 E. I. Du Pont De Nemours And Company Catalytic hydrogenation of 3-hydroxypropanal to 1,3-propanediol
TWI266760B (en) 2000-03-20 2006-11-21 Kvaerner Process Tech Ltd Process for the preparation of propane-1,3-diol
EP1179524A1 (en) 2000-08-10 2002-02-13 Kvaerner Process Technology Limited Process for the carbonylation of oxiranes
DE50006894D1 (de) * 2000-10-25 2004-07-29 Du Pont Verfahren zur Herstellung von 1,3-Propandiol
US6617478B2 (en) 2000-11-29 2003-09-09 Samsung Electronics Co., Ltd. Process for preparing a 1,3-alkandiol from 3-hydroxyester
EP1211234A3 (en) 2000-11-29 2003-11-26 Samsung Electronics Co., Ltd. Process for preparing 1,3-alkandiols from 3-hydroxyesters
US6693222B2 (en) 2002-02-12 2004-02-17 E. I. Du Pont De Nemours And Company Process for splitting water-soluble ethers
AR041460A1 (es) 2002-10-03 2005-05-18 Shell Int Research Reduccion de la viscosidad de los productos secundarios de alto peso molecular en la produccion de 1,3- propanodiol
WO2004061169A1 (en) * 2002-12-23 2004-07-22 E. I. Du Pont De Nemours And Company Poly(trimethylene terephthalate) bicomponent fiber process
MXPA05008920A (es) * 2003-02-24 2005-10-05 Shell Int Research Purificacion de 1,3-propandiol mediante destilacion.
US7323539B2 (en) * 2003-05-06 2008-01-29 E. I. Du Pont De Nemours And Company Polytrimethylene ether glycol and polytrimethylene ether ester with excellent quality
US7084311B2 (en) * 2003-05-06 2006-08-01 E. I. Du Pont De Nemours And Company Hydrogenation of chemically derived 1,3-propanediol
JP4814794B2 (ja) * 2003-05-06 2011-11-16 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 生物学的に生産された１，３−プロパンジオールの精製
US7342142B2 (en) 2003-05-06 2008-03-11 E.I. Du Pont De Nemours And Company Hydrogenation of polytrimethylene ether glycol
US20070035057A1 (en) * 2003-06-26 2007-02-15 Chang Jing C Poly(trimethylene terephthalate) bicomponent fiber process
MXPA06003819A (es) * 2003-10-07 2006-08-11 Shell Int Research Proceso para la produccion de 1,3-propanodiol por hidrogenacion catalitica de 3-hidroxipropanal en la presencia de un co-catalizador de hidratacion.
TW200536821A (en) 2004-02-05 2005-11-16 Showa Denko Kk Production process of 3-alkoxy-1-propanols, and 3-alkoxy-1-propanols obtained by the production process
US20080103217A1 (en) * 2006-10-31 2008-05-01 Hari Babu Sunkara Polyether ester elastomer composition
US7074969B2 (en) * 2004-06-18 2006-07-11 E.I. Du Pont De Nemours And Company Process for preparation of polytrimethylene ether glycols
US20060041039A1 (en) * 2004-08-20 2006-02-23 Gyorgyi Fenyvesi Fluorescent poly(alkylene terephthalate) compositions
US7358211B2 (en) * 2004-11-24 2008-04-15 E.I. Du Pont De Nemours And Company Catalyst for the production of 1,3-propanediol by catalytic hydrogenation of 3-hydroxypropanal
EP2270065A3 (en) 2004-12-21 2011-03-09 E. I. du Pont de Nemours and Company Poly(trimethylene terephthalate) composition and shaped articles prepared therefrom
US7396896B2 (en) * 2004-12-21 2008-07-08 E.I. Dupont De Nemours And Company Poly(trimethylene terephthalate) composition and shaped articles prepared therefrom
US20060189711A1 (en) * 2005-02-23 2006-08-24 Ng Howard C Silicon-containing polytrimethylene homo- or copolyether composition
US7629396B2 (en) * 2005-02-23 2009-12-08 E.I. Du Pont De Nemours And Company Silicon-containing polytrimethylene homo- for copolyether composition
US20060247378A1 (en) * 2005-05-02 2006-11-02 Sunkara Hari B Thermoplastic elastomer blend, method of manufacture and use thereof
US7244790B2 (en) * 2005-05-02 2007-07-17 E.I. Du Pont De Nemours And Company Thermoplastic elastomer blend, method of manufacture and use thereof
US7157607B1 (en) 2005-08-16 2007-01-02 E. I. Du Pont De Nemours And Company Manufacture of polytrimethylene ether glycol
US7161045B1 (en) 2005-08-16 2007-01-09 E. I. Du Pont De Nemours And Company Process for manufacture of polytrimethylene ether glycol
US7357985B2 (en) * 2005-09-19 2008-04-15 E.I. Du Pont De Nemours And Company High crimp bicomponent fibers
US20070129524A1 (en) * 2005-12-06 2007-06-07 Sunkara Hari B Thermoplastic polyurethanes comprising polytrimethylene ether soft segments
US20070128459A1 (en) * 2005-12-07 2007-06-07 Kurian Joseph V Poly(trimethylene terephthalate)/poly(alpha-hydroxy acid) films
US7666501B2 (en) * 2005-12-07 2010-02-23 E. I. Du Pont De Nemours And Company Poly(trimethylene terephthalate)/poly(alpha-hydroxy acid) bi-constituent filaments
US20070129503A1 (en) * 2005-12-07 2007-06-07 Kurian Joseph V Poly(trimethylene terephthalate)/poly(alpha-hydroxy acid) molded, shaped articles
US7388115B2 (en) * 2006-01-20 2008-06-17 E. I. Du Pont De Nemours And Company Manufacture of polytrimethylene ether glycol
US7164046B1 (en) 2006-01-20 2007-01-16 E. I. Du Pont De Nemours And Company Manufacture of polytrimethylene ether glycol
JP2007230979A (ja) * 2006-03-03 2007-09-13 Showa Denko Kk １，３−プロパンジオールの製造方法
US20080039582A1 (en) * 2006-07-28 2008-02-14 Hari Babu Sunkara Polytrimethylene ether-based polyurethane ionomers
US7531593B2 (en) 2006-10-31 2009-05-12 E.I. Du Pont De Nemours And Company Thermoplastic elastomer blend composition
US20080108845A1 (en) * 2006-11-07 2008-05-08 Hari Babu Sunkara Polytrimethylene ether glycol esters
US20080135662A1 (en) * 2006-12-06 2008-06-12 Chang Jing C Melt-spun elastoester multifilament yarns
US7714174B2 (en) * 2007-03-27 2010-05-11 E. I. Du Pont De Nemours And Company Lower-color polytrimethylene ether glycol using hydride compounds
US8703681B2 (en) 2007-08-24 2014-04-22 E I Du Pont De Nemours And Company Lubrication oil compositions
KR20100061813A (ko) * 2007-08-24 2010-06-09 이 아이 듀폰 디 네모아 앤드 캄파니 윤활유 조성물
MX2010002153A (es) * 2007-08-24 2010-03-18 Du Pont Composiciones de aceite de lubricacion.
WO2009029470A1 (en) * 2007-08-24 2009-03-05 E. I. Du Pont De Nemours And Company Lubrication oil compositions
BRPI0815315A2 (pt) * 2007-08-24 2017-05-09 Du Pont composição de oleo lubrificante
US7919017B2 (en) * 2007-11-12 2011-04-05 E. I. Du Pont De Nemours And Company Electrical insulation fluids for use in electrical apparatus
CN102264797A (zh) * 2008-12-23 2011-11-30 纳幕尔杜邦公司 聚(三亚甲基醚)二醇的丙烯酸酯和甲基丙烯酸酯的制备方法
MX2011006734A (es) * 2008-12-23 2011-07-13 Du Pont Esteres acrilicos y metacrilicos de glicol de eter de politrimetileno.
CN102264781A (zh) * 2008-12-23 2011-11-30 纳幕尔杜邦公司 聚(三亚甲基醚)二醇的(甲基)丙烯酸酯及其用途
US20100267994A1 (en) * 2009-04-16 2010-10-21 E. I. Du Pont De Nemours And Company Processes for preparing polytrimethylene glycol using ion exchange resins
US8247526B2 (en) 2010-12-20 2012-08-21 E I Du Pont De Nemours And Company Process for the preparation of polyalkylene ether glycol
EP2702089B1 (en) 2011-04-26 2017-04-05 E. I. du Pont de Nemours and Company Processes for preparing polytrimethylene ether glycol
US8759559B2 (en) 2012-04-18 2014-06-24 E I Du Pont De Nemours And Company Processes for preparing polytrimethylene ether glycol esters
CN113354512B (zh) * 2021-06-04 2022-09-09 江苏扬农化工集团有限公司 一种3,3’-氧双-1-丙醇水解制备1,3-丙二醇的方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE898894C (de) * 1941-12-05 1953-12-07 Basf Ag Verfahren zur Gewinnung niedrigermolekularer Polyaethylenglykole oder einfacher AEthylenglykole aus hoehermolekularen Polyaethylenglykolen
US4254290A (en) * 1979-12-20 1981-03-03 General Electric Company Acidic mixed oxide catalytic de-alkylation of tertiary-alkyl-ether-alkanols
US4806658A (en) * 1982-11-15 1989-02-21 The Dow Chemical Company Cleavage of polyethylene glycol ethers by hydrolysis
DE3926136A1 (de) * 1989-08-08 1991-02-14 Degussa Verfahren zur herstellung von 1,3-propandiol
DE4038192A1 (de) * 1990-11-30 1992-06-04 Degussa Verfahren zur herstellung von 1,3-propandiol
US5093537A (en) * 1991-07-24 1992-03-03 Hoechst Celanese Corporation Method for the manufacture of 1,3-propanediol

Also Published As

Publication number Publication date
JP3380295B2 (ja) 2003-02-24
CA2100229C (en) 2006-11-14
CA2100229A1 (en) 1994-01-11
US5364987A (en) 1994-11-15
KR100276538B1 (ko) 2000-12-15
EP0577972A1 (de) 1994-01-12
DE4222708A1 (de) 1994-01-13
TW277056B (ko) 1996-06-01
EP0577972B1 (de) 1996-01-24
ATE133402T1 (de) 1996-02-15
DE59301494D1 (de) 1996-03-07
JPH06157378A (ja) 1994-06-03

Similar Documents

Publication Publication Date Title
KR940002207A (ko) 1,3-프로판디올의 제조방법
US5523426A (en) Integrated process for epoxidation
JP4695810B2 (ja) フェノールの製造において使用されるクメンを製造する方法
JP2951510B2 (ja) クメンヒドロペルオキシドの二段階分解
AU2002216112A1 (en) Preparation of oxirane compounds
EP1366031A2 (en) Process for preparing oxirane compounds
US5354917A (en) Use of supported rhodium catalysts in the preparation of tertiary butyl alcohol from tertiary butyl hydroperoxide
JP3078407B2 (ja) プロピレンオキシドの精製方法
KR100385627B1 (ko) 통합된에폭시화공정
US6166263A (en) Processes for the manufacture of acrolein
US4605795A (en) Continuous process for the production of pentanediol-1,2
US6187963B1 (en) Processes for the manufacture of acrolein derivatives
EP0599883B1 (en) Continuous process for the preparation of 2-ethyl-2-(hydroxymethyl)hexanal and 2-butyl-2-ethyl-1,3-propanediol
US6972346B2 (en) Solid acid catalyzed reactive stripping of impurities formed during the production of 1, 3-propanediol
US4005112A (en) Multistep method for preparation of tetrahydrofuran starting from propylene, oxygen and a carboxylic acid
EP1666443B1 (en) Process for producing cumene and process for propylene oxide production including the production process
US2862978A (en) Synthetic glycerine production with intermediate removal of acrolein
JP3285439B2 (ja) 反応粗液の製造法および１，３−ブチレングリコ−ルの製造法
US5741952A (en) Catalytic decomposition of peroxides to purify a methyl tertiary butyl ether recycle stream
US5414163A (en) Use of titania or zirconia in the preparation of tertiary butyl alcohol from tertiary butyl hydroperoxide
JPH05255135A (ja) イソブチレンの製法
JP2006504789A (ja) １，３−プロパンジオールの生成中に形成される不純物の除去
EP0004732A1 (en) Preparation of 2-phenylethanol and 2-phenylethyl acetate
US5354925A (en) Use of supported lead oxide catalyst in the preparation of tertiary butyl alcohol from tertiary butyl hydroperoxide
JPH05229972A (ja) フェノール及びメチルエチルケトンの製造方法

Legal Events

Date Code Title Description
A201 Request for examination
N231 Notification of change of applicant
E902 Notification of reason for refusal
E701 Decision to grant or registration of patent right
GRNT Written decision to grant
FPAY Annual fee payment

Payment date: 20040924

Year of fee payment: 5

LAPS Lapse due to unpaid annual fee