ES2194356T3 - Procedimiento para preparar gamma-butirolactona, butano-1,4-diol y tetrahidrofurano. - Google Patents

Procedimiento para preparar gamma-butirolactona, butano-1,4-diol y tetrahidrofurano.

Info

Publication number
ES2194356T3
ES2194356T3 ES98951579T ES98951579T ES2194356T3 ES 2194356 T3 ES2194356 T3 ES 2194356T3 ES 98951579 T ES98951579 T ES 98951579T ES 98951579 T ES98951579 T ES 98951579T ES 2194356 T3 ES2194356 T3 ES 2194356T3
Authority
ES
Spain
Prior art keywords
carbon atoms
alkyl
maleate
hydrogenation
esters
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.)
Expired - Lifetime
Application number
ES98951579T
Other languages
English (en)
Inventor
Michael William Marshall Tuck
Michael Anthony Wood
Andrew George Hiles
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Application granted granted Critical
Publication of ES2194356T3 publication Critical patent/ES2194356T3/es
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/32—Oxygen atoms
    • C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D315/00—Heterocyclic compounds containing rings having one oxygen atom as the only ring hetero atom according to more than one of groups C07D303/00 - C07D313/00
    • 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
    • C07C29/147—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 carboxylic acids or derivatives thereof
    • C07C29/149—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 carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
    • 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
    • C07C31/207—1,4-Butanediol; 1,3-Butanediol; 1,2-Butanediol; 2,3-Butanediol
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/06—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • C07D307/08—Preparation of tetrahydrofuran

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Furan Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Un procedimiento para la producción de al menos un compuesto de 4 átomos de carbono seleccionado de butano-1, 4-diol, -butirolactona y tetrahidrofurano, que incluye la etapa de hidrogenación en fase de vapor de un maleato de di-alquilo(de 1 a 4 átomos de carbono) en presencia de un catalizador de hidrogenación de éster en partículas, procedimiento que comprende: (a) poner en contacto una corriente en fase de vapor que contiene vapor de anhídrido maleico, vapor de agua y óxidos de carbono en una zona de absorción con un éster de alto punto de ebullición como disolvente, para formar de ese modo una solución de anhídrido maleico en el éster de alto punto de ebullición, teniendo dicho éster de alto punto de ebullición un punto de ebullición a presión atmosférica que es al menos 30ºC superior que el del maleato de di-(alquilo de 1 a 4 átomos de carbono) y seleccionándose de ésteres di-(alquílicos de 1 a 4 átomos de carbono) de ácidos alquildicarboxílicos que contienen hasta 13 átomos de carbono,ésteres mono- y di- (alquílicos de 10 a 18 átomos de carbono) de ácido maleico, ácido fumárico, ácido succínico y mezclas de los mismos, ésteres (alquílicos de 1 a 4 átomos de carbono) de ácidos naftalenomonocarboxílicos, ésteres tri- (alquílicos de 1 a 4 átomos de carbono) de ácidos tricarboxílicos aromáticos y ésteres di-(alquílicos de 1 a 4 átomos de carbono) de ácido isoftálico; (b) recuperar de la zona de absorción una corriente gaseosa residual; (c) hacer reaccionar anhídrido maleico en la solución de anhídrido maleico de la etapa (a) bajo condiciones de esterificación en una zona de esterificación con un alcanol de 1 a 4 átomos de carbono para formar el maleato de di-(alquilo de 1 a 4 átomos de carbono) correspondiente; (d) recuperar de la zona de esterificación una solución del maleato de di-(alquilo de 1 a 4 átomos de carbono) en el éster de alto punto de ebullición; (e) poner en contacto la solución del maleato de di- (alquilo de 1 a 4 átomos de carbono) en el éster de alto puntode ebullición con una corriente gaseosa que contiene hidrógeno, para separar de ese modo por arrastre maleato de di-(alquilo de 1 a 4 átomos de carbono) del mismo y formar una corriente en fase de vapor que comprende hidrógeno y maleato de di-(alquilo de 1 a 4 átomos de carbono); (f) poner en contacto el material de la corriente en fase de vapor la etapa (e) en una zona de hidrogenación bajo condiciones de hidrogenación de ésteres con un catalizador de hidrogenación de ésteres heterogéneo, para convertir de ese modo maleato de di-(alquilo de 1 a 4 átomos de carbono) mediante hidrogenación en al menos un compuesto de 4 átomos de carbono seleccionado de butano- 1, 4-diol, -butirolactona y tetrahidrofurano; y (g) recuperar de la zona de hidrogenación una corriente de productos que contiene dicho al menos un compuesto de 4 átomos de carbono.
ES98951579T 1997-11-13 1998-11-02 Procedimiento para preparar gamma-butirolactona, butano-1,4-diol y tetrahidrofurano. Expired - Lifetime ES2194356T3 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GBGB9724004.8A GB9724004D0 (en) 1997-11-13 1997-11-13 Process

Publications (1)

Publication Number Publication Date
ES2194356T3 true ES2194356T3 (es) 2003-11-16

Family

ID=10822029

Family Applications (1)

Application Number Title Priority Date Filing Date
ES98951579T Expired - Lifetime ES2194356T3 (es) 1997-11-13 1998-11-02 Procedimiento para preparar gamma-butirolactona, butano-1,4-diol y tetrahidrofurano.

Country Status (19)

Country Link
US (1) US6239292B1 (es)
EP (1) EP1030830B1 (es)
JP (1) JP4205857B2 (es)
KR (1) KR100520472B1 (es)
CN (1) CN1125026C (es)
AR (1) AR013763A1 (es)
AU (1) AU751187B2 (es)
BR (1) BR9814185A (es)
CA (1) CA2309997A1 (es)
DE (1) DE69811935T2 (es)
ES (1) ES2194356T3 (es)
GB (1) GB9724004D0 (es)
ID (1) ID25468A (es)
MY (1) MY127875A (es)
NO (1) NO20002473D0 (es)
SA (1) SA99191005B1 (es)
TW (1) TW444007B (es)
WO (1) WO1999025678A1 (es)
ZA (1) ZA989588B (es)

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DE19808846A1 (de) * 1998-03-03 1999-09-09 Huels Chemische Werke Ag Verfahren zur Herstellung von Lactonen
DE19818340A1 (de) * 1998-04-23 1999-10-28 Basf Ag Verfahren zur Herstellung von Gemischen aus 1,4-Butandiol, Tetrahydrofuran und gamma-Butyrolacton
US6194587B1 (en) * 1999-08-19 2001-02-27 Scientific Design Company, Inc. Production of maleic anhydride
GB0325530D0 (en) 2003-10-31 2003-12-03 Davy Process Techn Ltd Process
GB0325526D0 (en) 2003-10-31 2003-12-03 Davy Process Techn Ltd Process
GB0421928D0 (en) 2004-10-01 2004-11-03 Davy Process Techn Ltd Process
CN100400162C (zh) * 2006-10-19 2008-07-09 复旦大学 一种用于马来酸二甲酯加氢制备1,4-丁二醇的催化剂的制备方法
KR101001332B1 (ko) 2008-06-12 2010-12-14 이수화학 주식회사 감마부티로락톤의 제조방법
KR101042091B1 (ko) * 2009-01-13 2011-06-16 한국항공우주산업 주식회사 인서트 플러그 체결 치구 및 그를 이용한 인서트 플러그 체결 방법
GB0906031D0 (en) * 2009-04-07 2009-05-20 Davy Process Techn Ltd Process
KR20150080037A (ko) 2011-06-08 2015-07-08 바이오젠 엠에이 인코포레이티드 고순도 및 결정질 다이메틸 푸마레이트의 제조 방법
EP2782893B1 (en) 2011-11-25 2017-08-23 Conser SPA Process for producing 1,4-butanediol, gamma-butyrolactone and tetrahydrofuran by hydrogenating dialkyl maleate in mixed liquid/vapor phase
GB201504948D0 (en) * 2015-03-24 2015-05-06 Johnson Matthey Davy Technologies Ltd Process
CN107473966B (zh) * 2017-08-29 2021-01-05 南京雪郎化工科技有限公司 一种马来酸二甲酯的生产方法
EP4188903B1 (en) 2021-03-12 2024-01-03 Conser S.P.A. Process for the co-production of dialkyl succinate and 1,4-butanediol by hydrogenating dialkyl maleate in two stages
CN117580827A (zh) * 2021-06-25 2024-02-20 Cj第一制糖株式会社 用于生产四氢呋喃、γ-丁内酯或1,4-丁二醇的方法
KR102604948B1 (ko) * 2021-06-25 2023-11-23 씨제이제일제당(주) 테트라하이드로퓨란, 감마부티로락톤 또는 1,4-부탄디올의 제조 방법
US20240287011A1 (en) * 2021-06-25 2024-08-29 Cj Cheiljedang Corporation Method for producing tetrahydrofuran, gamma-butyrolactone, or 1,4-butanediol
EP4549617A1 (en) 2023-10-31 2025-05-07 Basf Se Preparation of saturated or ethylenically unsaturated (cyclo)aliphatic compounds by hydrogenation of ethylenically or acetylenically unsaturated (cyclo)aliphatic compounds using hydrogen with low deuterium content

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Also Published As

Publication number Publication date
ZA989588B (en) 1999-06-01
ID25468A (id) 2000-10-05
NO20002473L (no) 2000-05-12
KR100520472B1 (ko) 2005-10-11
US6239292B1 (en) 2001-05-29
SA99191005B1 (ar) 2006-10-02
WO1999025678A1 (en) 1999-05-27
AU751187B2 (en) 2002-08-08
CN1280558A (zh) 2001-01-17
EP1030830A1 (en) 2000-08-30
TW444007B (en) 2001-07-01
KR20010032015A (ko) 2001-04-16
EP1030830B1 (en) 2003-03-05
DE69811935D1 (de) 2003-04-10
JP2001523657A (ja) 2001-11-27
AR013763A1 (es) 2001-01-10
NO20002473D0 (no) 2000-05-12
AU9753898A (en) 1999-06-07
DE69811935T2 (de) 2004-02-12
CA2309997A1 (en) 1999-05-27
GB9724004D0 (en) 1998-10-21
CN1125026C (zh) 2003-10-22
JP4205857B2 (ja) 2009-01-07
MY127875A (en) 2006-12-29
BR9814185A (pt) 2000-10-03

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