FI127020B - Selektiivinen menetelmä levuliinihapon konversioon gammavalerolaktoniksi - Google Patents

Selektiivinen menetelmä levuliinihapon konversioon gammavalerolaktoniksi Download PDF

Info

Publication number
FI127020B
FI127020B FI20156006A FI20156006A FI127020B FI 127020 B FI127020 B FI 127020B FI 20156006 A FI20156006 A FI 20156006A FI 20156006 A FI20156006 A FI 20156006A FI 127020 B FI127020 B FI 127020B
Authority
FI
Finland
Prior art keywords
acid
reaction
conversion
gammavalerolactone
levulinic acid
Prior art date
Application number
FI20156006A
Other languages
English (en)
Swedish (sv)
Other versions
FI20156006A (fi
Inventor
Sami Toppinen
Original Assignee
Neste Oyj
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 Neste Oyj filed Critical Neste Oyj
Priority to FI20156006A priority Critical patent/FI127020B/fi
Priority to CA2951451A priority patent/CA2951451C/en
Priority to ES16204213T priority patent/ES2726286T3/es
Priority to EP16204213.9A priority patent/EP3184517B1/en
Priority to BR102016030289-7A priority patent/BR102016030289B1/pt
Priority to US15/388,924 priority patent/US9914714B2/en
Priority to CN201611204871.0A priority patent/CN106946819B/zh
Publication of FI20156006A publication Critical patent/FI20156006A/fi
Application granted granted Critical
Publication of FI127020B publication Critical patent/FI127020B/fi

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring
    • 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
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B37/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving either the formation of a carbon-to-carbon bond between two carbon atoms not directly linked already or the disconnection of two directly linked carbon atoms
    • C07B37/10—Cyclisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
    • 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

Claims (10)

1. Prosessi gammavalerolaktonin valmistamiseksi kaksivaiheisessa menetelmässä, jossa • ensimmäisessä vaiheessa levuliinihappo konvertoidaan katalyyttisellä vedytyksellä 4-hydroksipentaanihapoksi ja gammavalerolaktoniksi, ja • toisessa vaiheessa mainitun 4-hydroksipentaanihapon annetaan reagoida gammavalerolaktoniksi vedytystä estävissä olosuhteissa.
2. Patenttivaatimuksen 1 mukainen prosessi, jolloin toisessa vaiheessa mainitun 4-hydroksipentaanihapon reagoinnissa gammavalerolaktoniksi reaktio-olosuhteet käsittävät lämpötilan vähintään 100 °C.
3. Patenttivaatimuksen 1 tai 2 mukainen prosessi, jolloin toisessa vaiheessa mainitun 4-hydroksipentaanihapon reagoinnissa gammavalerolaktoniksi lämpötila on 130 - 200 °C ja edullisemmin 150 - 170 °C.
4. Patenttivaatimuksen 1 mukainen prosessi, jolloin toisessa vaiheessa mainitun 4-hydroksipentaanihapon reagoinnissa gammavalerolaktoniksi reaktio-olosuhteet käsittävät happokatalyytin.
5. Patenttivaatimuksen 4 mukainen prosessi, jolloin lämpötila mainitussa toisessa vaiheessa 4-hydroksipentaanihapon reagoimiseksi gammavalerolaktoniksi on 100 - 150 °C ja edullisemmin 100 - 120 °C.
6. Jonkin edeltävän patenttivaatimuksen mukainen prosessi, jolloin mainitun ensimmäisen vaiheen levuliinihapon katalyyttisen vedytyksen reaktio-olosuhteet käsittävät vähintään yhden seuraavista • lämpötila 60 - 120 °C, edullisesti 80 - 110 °C • katalyytti, joka on valittu alkuaineiden jaksollisen järjestelmän ryhmän VIII metalleista tai niiden yhdistelmistä.
7. Patenttivaatimuksen 6 mukainen prosessi, jolloin katalyyttisen vedytyksen katalyytti on valittu Co, Ni, Ru, Pd, Pt tai niiden yhdistelmien joukosta.
8. Jonkin patenttivaatimuksista 1-7 mukainen prosessi, jolloin vedytystä estävät olosuhteet toiseen vaiheeseen saadaan aikaan ajamalla levuliinihapon konversio ensimmäisessä reaktorissa ja 4-hydroksipentaanihapon konversio toisessa reaktorissa.
9. Jonkin patenttivaatimuksista 1-8 mukainen prosessi, jolloin vedytystä estävät olosuhteet toiseen vaiheeseen saadaan aikaan alentamalla vetypainetta levuliinihapon konversion jälkeen.
10. Jonkin patenttivaatimuksista 1-8 mukainen prosessi, jolloin vedytystä estävät olosuhteet toiseen vaiheeseen saadaan aikaan käyttäen levuliinihapon konversiossa vetykaasuatmosfääriä ja 4-hydroksypentaanihapon konversiossa inerttikaasuatmosfääriä.
FI20156006A 2015-12-23 2015-12-23 Selektiivinen menetelmä levuliinihapon konversioon gammavalerolaktoniksi FI127020B (fi)

Priority Applications (7)

Application Number Priority Date Filing Date Title
FI20156006A FI127020B (fi) 2015-12-23 2015-12-23 Selektiivinen menetelmä levuliinihapon konversioon gammavalerolaktoniksi
CA2951451A CA2951451C (en) 2015-12-23 2016-12-12 A selective process for conversion of levulinic acid to gamma-valerolactone
ES16204213T ES2726286T3 (es) 2015-12-23 2016-12-15 Un proceso selectivo para la conversión de ácido levulínico en gamma-valerolactona
EP16204213.9A EP3184517B1 (en) 2015-12-23 2016-12-15 A selective process for conversion of levulinic acid to gammavalerolactone
BR102016030289-7A BR102016030289B1 (pt) 2015-12-23 2016-12-22 Processo seletivo para conversão de ácido levulínico em gama-valerolactona
US15/388,924 US9914714B2 (en) 2015-12-23 2016-12-22 Selective process for conversion of levulinic acid to gammavalerolactone
CN201611204871.0A CN106946819B (zh) 2015-12-23 2016-12-23 将乙酰丙酸转化成γ-戊内酯的选择性方法

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FI20156006A FI127020B (fi) 2015-12-23 2015-12-23 Selektiivinen menetelmä levuliinihapon konversioon gammavalerolaktoniksi

Publications (2)

Publication Number Publication Date
FI20156006A FI20156006A (fi) 2017-06-24
FI127020B true FI127020B (fi) 2017-09-29

Family

ID=57799450

Family Applications (1)

Application Number Title Priority Date Filing Date
FI20156006A FI127020B (fi) 2015-12-23 2015-12-23 Selektiivinen menetelmä levuliinihapon konversioon gammavalerolaktoniksi

Country Status (7)

Country Link
US (1) US9914714B2 (fi)
EP (1) EP3184517B1 (fi)
CN (1) CN106946819B (fi)
BR (1) BR102016030289B1 (fi)
CA (1) CA2951451C (fi)
ES (1) ES2726286T3 (fi)
FI (1) FI127020B (fi)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111135828B (zh) * 2020-01-02 2022-10-25 云南大学 一种催化剂及其该催化剂的应用、制备、性能测试方法
CN113546633B (zh) * 2021-07-27 2022-07-01 云南大学 一种镨基磁性催化剂及其制备方法和应用

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2368366A (en) * 1942-08-21 1945-01-30 Monsanto Chemicals Process for the production of lactones
US2813900A (en) 1953-08-05 1957-11-19 Quaker Oats Co Process for producing levulinic acid
US3701789A (en) 1970-10-15 1972-10-31 Commw Of Puerto Rico Process for jointly producing furfural and levulinic acid from bagasse and other lignocellulosic materials
US4533743A (en) 1983-12-16 1985-08-06 Atlantic Richfield Company Furfural process
US4897497A (en) 1988-04-26 1990-01-30 Biofine Incorporated Lignocellulose degradation to furfural and levulinic acid
US5608105A (en) 1995-06-07 1997-03-04 Biofine Incorporated Production of levulinic acid from carbohydrate-containing materials
ATE318803T1 (de) * 2000-08-24 2006-03-15 Union Carbide Chem Plastic Verfahren zur herstellung von laktonen
KR20030082984A (ko) 2001-03-16 2003-10-23 이 아이 듀폰 디 네모아 앤드 캄파니 레불린산으로부터 5-메틸부티로락톤의 제조 방법
CN101805316A (zh) 2010-04-22 2010-08-18 复旦大学 一种用负载型铱催化剂制备γ-戊内酯的方法
EP2611764A4 (en) * 2010-08-30 2016-12-14 Arzeda Corp FERMENTATION ROUTE FOR THE PRODUCTION OF LÉVULINIC ACID, LEVULINATE ESTERS, VALÉROLACTONE, AND CERTAIN OF THEIR DERIVATIVES
WO2012041990A1 (en) 2010-09-30 2012-04-05 Shell Internationale Research Maatschappij B.V. Process for producing furfural
WO2012175439A1 (en) 2011-06-21 2012-12-27 Dsm Ip Assets B.V. Process to produce valerolactone from levulinic acid
PL2537841T3 (pl) 2011-06-22 2014-02-28 Dsm Ip Assets Bv Ciągłe wytwarzanie furfuralu oraz kwasu lewulinowego
CN102558108B (zh) 2011-12-22 2014-07-16 南开大学 用铱-钳形配体络合物催化剂制备γ-戊内酯的方法
US20130168227A1 (en) 2011-12-28 2013-07-04 E I Du Pont De Nemours And Company Process for the production of furfural
CN102617519B (zh) 2012-03-05 2014-08-13 中国石油大学(华东) 由乙酰丙酸加氢制备γ-戊内酯的方法
CN102659723B (zh) 2012-04-27 2016-02-03 北京博能康成科技有限公司 用高粗纤维植物农副产品制备糠醛的方法
BR112015026960B1 (pt) 2013-04-27 2021-07-27 The Regents Of The University Of California Métodos para a produção de intermediários reativos a partir de biomassa e para a solubilização e conversão catalítica combinadas de biomassa
US9346731B2 (en) 2013-09-18 2016-05-24 Georgia-Pacific LLC Method for producing levulinic acid from sludge and lignocellulosic biomass
EP3262032A1 (en) * 2015-02-24 2018-01-03 DSM IP Assets B.V. Process for the preparation of gamma valerolactone from levulinic acid

Also Published As

Publication number Publication date
BR102016030289A2 (pt) 2017-06-27
EP3184517B1 (en) 2019-03-27
US20170183321A1 (en) 2017-06-29
FI20156006A (fi) 2017-06-24
CA2951451C (en) 2022-09-06
CN106946819A (zh) 2017-07-14
CA2951451A1 (en) 2017-06-23
BR102016030289B1 (pt) 2021-04-27
EP3184517A1 (en) 2017-06-28
US9914714B2 (en) 2018-03-13
ES2726286T3 (es) 2019-10-03
CN106946819B (zh) 2022-10-04

Similar Documents

Publication Publication Date Title
dos Santos et al. Electrochemistry for the generation of renewable chemicals: electrochemical conversion of levulinic acid
EP3154927B1 (en) Method for producing muconic acids and furans from aldaric acids
KR101325084B1 (ko) 글리세롤의 기상 수소첨가 방법
DK3145902T3 (en) PROCEDURE FOR CONTINUOUS PREPARATION OF ETHYLENGYLYCOL FROM CARBOHYDRATES
EP2537840B1 (en) Process to produce valerolactone from levulinic acid
CN106458951B (zh) 糠醛的制造方法和呋喃的制造方法
FR2925046A1 (fr) Procede d'obtention d'alcool a partir d'un aldehyde
CA2714574A1 (en) Process for preparing 6-hydroxycaproic esters
FI127020B (fi) Selektiivinen menetelmä levuliinihapon konversioon gammavalerolaktoniksi
CN108026058B (zh) 由呋喃制造1,4-丁二醇和四氢呋喃的方法
US8809592B2 (en) Process for producing DIBK
CN108329203B (zh) 一种甘油酸制备3-羟基丙酸的方法
US9475786B2 (en) Method for synthesising 2,5-di(hydroxymethyl)furan and 2,5-di(hydroxymethyl)tetrahydrofuran by selective hydrogenation of furan-2,5-dialdehyde
KR20150001667A (ko) 알릴 알코올의 제조방법 및 이에 의하여 제조된 알릴 알코올
KR101639487B1 (ko) 공정 단순화를 위한 트랜스-1,4-사이클로헥산디메탄올 제조장치
KR101632483B1 (ko) 호모세린계 화합물의 처리 공정
EP3774753B1 (en) Conversion of 1,2,5,6-hexanetetrol (hto) to tetrahydrofuran dicarboxylic acid (thfdca)
JP6369828B2 (ja) ヒドロキシメチルフルフラールの還元方法
KR20230065738A (ko) 이소부테놀의 제조방법
CN115697982A (zh) 四氢呋喃-2-羧酸的制造方法
Palkovits Chemo-catalytic valorization of cellulose

Legal Events

Date Code Title Description
FG Patent granted

Ref document number: 127020

Country of ref document: FI

Kind code of ref document: B