CA2551223A1 - Integrated process for acetic acid and methanol - Google Patents
Integrated process for acetic acid and methanol Download PDFInfo
- Publication number
- CA2551223A1 CA2551223A1 CA002551223A CA2551223A CA2551223A1 CA 2551223 A1 CA2551223 A1 CA 2551223A1 CA 002551223 A CA002551223 A CA 002551223A CA 2551223 A CA2551223 A CA 2551223A CA 2551223 A1 CA2551223 A1 CA 2551223A1
- Authority
- CA
- Canada
- Prior art keywords
- stream
- methanol
- acetic acid
- preceeding
- syngas
- 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
- C07C29/15—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 oxides of carbon exclusively
- C07C29/151—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 oxides of carbon exclusively with hydrogen or hydrogen-containing gases
- C07C29/1516—Multisteps
- C07C29/1518—Multisteps one step being the formation of initial mixture of carbon oxides and hydrogen for synthesis
-
- 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
- C07C29/15—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 oxides of carbon exclusively
- C07C29/151—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 oxides of carbon exclusively with hydrogen or hydrogen-containing gases
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
- C07C51/12—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on an oxygen-containing group in organic compounds, e.g. alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/08—Acetic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
- C07C67/05—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Abstract
An integrated process for making methanol, acetic acid, and a product from an associated process is disclosed. Syngas (120) is produced by combined steam reforming (109) and autothermal reforming (118) of natural gas (102) where a portion (112) of the natural gas bypasses the steam reformer (109) and is blended with the steam reformer effluent for supply to the autothermal reformer (ATR) (118) with C02 recycle (110). A portion of the syngas is fed to C02 removal (122) to obtain the recycle C02 and cold box (130) to obtain a hydrogen stream (131) and a CO stream (135). The remaining syngas, hydrogen stream (131) and C02 from an associated process are fed to methanol synthesis (140), which produces methanol and a purge stream (124) supplied to the C02 removal unit. The methanol is supplied to an acetic acid unit (13)6 with the CO (135) to make acetic acid, which in turn is supplied to a VAM synthesis unit (148). Oxygen for both the ATR and VAM synthesis can be supplied by a common air separation unit (116), and utilities such as steam generation can further integrate the process.
Claims
CLAIMS:
[cl 1] A method for manufacturing methanol and acetic acid, characterized by the integrated steps of:
separating a hydrocarbon source into first and second hydrocarbon streams;
steam reforming the first hydrocarbon stream with steam to produce a reformed stream;
autothermal reforming of a mixture of the reformed stream and the second hydrocarbon stream with oxygen and carbon dioxide to produce a syngas stream;
separating a minor portion of the syngas stream into a carbon dioxide-rich stream, a hydrogen-rich stream, and a carbon monoxide-rich stream;
recycling the carbon dioxide-rich stream to the autothermal reforming;
compressing a remaining portion of the syngas stream, at least a portion of the hydrogen-rich stream to supply a makeup stream to a methanol synthesis loop to obtain a methanol product; and synthesizing acetic acid from at least a portion of the methanol product and the carbon monoxide-rich stream.
[cl 2] The method of claim 1, wherein the makeup stream has an SN between 2.0 and 2.1.
[cl 3] The method of any one of the preceeding claims, further comprising supplying a purge gas stream from the methanol synthesis loop to the separation step.
[cl 4] The method of any one of the preceeding claims, wherein the autothermal reformer is a single train autothermal reformer.
[cl 5] The method of any one of the preceeding claims, wherein the separation step includes supplying the minor portion of the syngas to a methane wash cold box unit.
[cl 6] The method of claim 5, wherein a flash gas from the separation step is recycled to the methanol synthesis loop.
[cl 7] The method of any one of claims 5 or 6, wherein a tail gas stream from the cold box is recycled as feed gas.
[cl 8] The method of any one of the preceeding claims, wherein carbon dioxide emissions are less than 10% of the total carbon input.
[cl 9] The method of any one of claims 1-7, wherein carbon dioxide emissions are less than 5 percent of the total carbon input.
[cl 10] The method of any one of the preceeding claims, wherein a first portion of the hydrogen-rich stream from the separation step is recycled to the methanol synthesis loop and a second portion is sent as feed to an associated process.
[cl 11] The method of any one of the preceeding claims, further comprising supplying a carbon dioxide stream from an associated process to supply the makeup stream.
[cl 12] The method of any one of claims 10 or 11, wherein the associated process uses the acetic acid as a reactant, uses the methanol product as a reactant, shares oxygen from a common air separation unit, shares common utilities, or a combination thereof.
[cl 13] The method of any one of claims 10-12, further comprising:
providing at least a portion of the acetic acid produced to a vinyl acetate monomer synthesis loop in the associated process;
combining the portion of the acetic acid with an ethylene source and oxygen to produce vinyl acetate monomer.
[cl 14] The method of claim 13, wherein a single air separation unit supplies oxygen to the associated process and the autothermal reformer.
[cl 15] The method of any one of the preceeding claims, wherein at least 10%
of the syngas stream is directed to the separation step.
[cl 16] The method of any one of the preceeding claims, wherein the methanol produced is between 1,000 and 30,000 tons/day.
[cl 17] The method of any one of the preceeding claims, wherein the acetic acid produced is between 500 and 6,000 metric tons/day.
[cl 18] The method of any preceding claim, further comprising importing a CO2-rich stream to the methanol synthesis loop.
[cl 19] The method of claim 13, further comprising importing a CO2-rich stream from the vinyl acetate monomer synthesis loop to the methanol synthesis loop.
[cl 20] The method of claim 18 or 19, wherein the hydrocarbon source comprises natural gas and a ratio of the imported CO2 stream to the hydrocarbon source is at least 0.05 kg CO2 per Nm3 natural gas.
[cl 21] The method of claim 20, wherein the ratio of the imported CO2 stream to the natural gas is at least 0.2 kg CO2 per Nm3 natural gas.
[cl 22] The method of claim 19, wherein the ratio of the imported CO2 to the natural gas is at least 0.23 kg CO2 per Nm3 natural gas.
[cl 23] The method of any one of the preceding claims, comprising:
diverting between 35 and 65% of the feed gas stream to the first stream;
and diverting between 35 and 65% of the feed gas stream to the second stream.
[cl 24] The method of any one of the preceding claims, comprising:
diverting 45 to 55% of the feed gas stream to the first stream; and diverting 45 to 55% of the feed gas stream to the second stream.
[cl 25] The method of any preceding claim wherein the separation step produces a tail gas stream enriched in inerts.
[cl 1] A method for manufacturing methanol and acetic acid, characterized by the integrated steps of:
separating a hydrocarbon source into first and second hydrocarbon streams;
steam reforming the first hydrocarbon stream with steam to produce a reformed stream;
autothermal reforming of a mixture of the reformed stream and the second hydrocarbon stream with oxygen and carbon dioxide to produce a syngas stream;
separating a minor portion of the syngas stream into a carbon dioxide-rich stream, a hydrogen-rich stream, and a carbon monoxide-rich stream;
recycling the carbon dioxide-rich stream to the autothermal reforming;
compressing a remaining portion of the syngas stream, at least a portion of the hydrogen-rich stream to supply a makeup stream to a methanol synthesis loop to obtain a methanol product; and synthesizing acetic acid from at least a portion of the methanol product and the carbon monoxide-rich stream.
[cl 2] The method of claim 1, wherein the makeup stream has an SN between 2.0 and 2.1.
[cl 3] The method of any one of the preceeding claims, further comprising supplying a purge gas stream from the methanol synthesis loop to the separation step.
[cl 4] The method of any one of the preceeding claims, wherein the autothermal reformer is a single train autothermal reformer.
[cl 5] The method of any one of the preceeding claims, wherein the separation step includes supplying the minor portion of the syngas to a methane wash cold box unit.
[cl 6] The method of claim 5, wherein a flash gas from the separation step is recycled to the methanol synthesis loop.
[cl 7] The method of any one of claims 5 or 6, wherein a tail gas stream from the cold box is recycled as feed gas.
[cl 8] The method of any one of the preceeding claims, wherein carbon dioxide emissions are less than 10% of the total carbon input.
[cl 9] The method of any one of claims 1-7, wherein carbon dioxide emissions are less than 5 percent of the total carbon input.
[cl 10] The method of any one of the preceeding claims, wherein a first portion of the hydrogen-rich stream from the separation step is recycled to the methanol synthesis loop and a second portion is sent as feed to an associated process.
[cl 11] The method of any one of the preceeding claims, further comprising supplying a carbon dioxide stream from an associated process to supply the makeup stream.
[cl 12] The method of any one of claims 10 or 11, wherein the associated process uses the acetic acid as a reactant, uses the methanol product as a reactant, shares oxygen from a common air separation unit, shares common utilities, or a combination thereof.
[cl 13] The method of any one of claims 10-12, further comprising:
providing at least a portion of the acetic acid produced to a vinyl acetate monomer synthesis loop in the associated process;
combining the portion of the acetic acid with an ethylene source and oxygen to produce vinyl acetate monomer.
[cl 14] The method of claim 13, wherein a single air separation unit supplies oxygen to the associated process and the autothermal reformer.
[cl 15] The method of any one of the preceeding claims, wherein at least 10%
of the syngas stream is directed to the separation step.
[cl 16] The method of any one of the preceeding claims, wherein the methanol produced is between 1,000 and 30,000 tons/day.
[cl 17] The method of any one of the preceeding claims, wherein the acetic acid produced is between 500 and 6,000 metric tons/day.
[cl 18] The method of any preceding claim, further comprising importing a CO2-rich stream to the methanol synthesis loop.
[cl 19] The method of claim 13, further comprising importing a CO2-rich stream from the vinyl acetate monomer synthesis loop to the methanol synthesis loop.
[cl 20] The method of claim 18 or 19, wherein the hydrocarbon source comprises natural gas and a ratio of the imported CO2 stream to the hydrocarbon source is at least 0.05 kg CO2 per Nm3 natural gas.
[cl 21] The method of claim 20, wherein the ratio of the imported CO2 stream to the natural gas is at least 0.2 kg CO2 per Nm3 natural gas.
[cl 22] The method of claim 19, wherein the ratio of the imported CO2 to the natural gas is at least 0.23 kg CO2 per Nm3 natural gas.
[cl 23] The method of any one of the preceding claims, comprising:
diverting between 35 and 65% of the feed gas stream to the first stream;
and diverting between 35 and 65% of the feed gas stream to the second stream.
[cl 24] The method of any one of the preceding claims, comprising:
diverting 45 to 55% of the feed gas stream to the first stream; and diverting 45 to 55% of the feed gas stream to the second stream.
[cl 25] The method of any preceding claim wherein the separation step produces a tail gas stream enriched in inerts.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/CY2004/000002 WO2005070855A1 (en) | 2004-01-22 | 2004-01-22 | Integrated process for acetic acid and methanol |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2551223A1 true CA2551223A1 (en) | 2005-08-04 |
CA2551223C CA2551223C (en) | 2011-05-03 |
Family
ID=34800359
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA2551223A Expired - Fee Related CA2551223C (en) | 2004-01-22 | 2004-01-22 | Integrated process for acetic acid and methanol |
Country Status (16)
Country | Link |
---|---|
US (1) | US7470811B2 (en) |
EP (1) | EP1708982A1 (en) |
JP (1) | JP4633741B2 (en) |
KR (2) | KR20100131528A (en) |
CN (1) | CN1906145B (en) |
AU (1) | AU2004314237B2 (en) |
BR (1) | BRPI0418477B1 (en) |
CA (1) | CA2551223C (en) |
MX (1) | MXPA06007682A (en) |
NO (1) | NO20063692L (en) |
NZ (1) | NZ548230A (en) |
PL (1) | PL209862B1 (en) |
RS (1) | RS20060418A (en) |
UA (1) | UA85579C2 (en) |
WO (1) | WO2005070855A1 (en) |
ZA (1) | ZA200605928B (en) |
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JP5539517B2 (en) * | 2009-08-14 | 2014-07-02 | サウディ ベーシック インダストリーズ コーポレイション | Combined reforming process for methanol production |
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CN201768471U (en) * | 2010-07-23 | 2011-03-23 | 镇海石化建安工程有限公司 | Low temperature methanol washing raw gas cooler |
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CA2919959C (en) | 2013-09-05 | 2022-05-03 | Praxair Technology, Inc. | Method and system for producing methanol using an integrated oxygen transport membrane based reforming system |
US9587189B2 (en) | 2013-10-01 | 2017-03-07 | Gas Technologies L.L.C. | Diesel fuel composition |
WO2015054223A2 (en) | 2013-10-07 | 2015-04-16 | Praxair Technology, Inc. | Ceramic oxygen transport membrane array reactor and reforming method |
CN105593162B (en) | 2013-10-08 | 2018-09-07 | 普莱克斯技术有限公司 | For the temperature controlled system and method in the reactor based on oxygen transport membrane |
US9556027B2 (en) | 2013-12-02 | 2017-01-31 | Praxair Technology, Inc. | Method and system for producing hydrogen using an oxygen transport membrane based reforming system with secondary reforming |
WO2015123246A2 (en) | 2014-02-12 | 2015-08-20 | Praxair Technology, Inc. | Oxygen transport membrane reactor based method and system for generating electric power |
US10822234B2 (en) | 2014-04-16 | 2020-11-03 | Praxair Technology, Inc. | Method and system for oxygen transport membrane enhanced integrated gasifier combined cycle (IGCC) |
EA201692175A1 (en) * | 2014-04-29 | 2017-06-30 | Хальдор Топсёэ А/С | METHOD OF OBTAINING METHANOL |
US9789445B2 (en) | 2014-10-07 | 2017-10-17 | Praxair Technology, Inc. | Composite oxygen ion transport membrane |
WO2016083434A1 (en) * | 2014-11-25 | 2016-06-02 | Haldor Topsøe A/S | A process for generation of synthesis gas by flue gas recycle |
US10441922B2 (en) | 2015-06-29 | 2019-10-15 | Praxair Technology, Inc. | Dual function composite oxygen transport membrane |
US10118823B2 (en) | 2015-12-15 | 2018-11-06 | Praxair Technology, Inc. | Method of thermally-stabilizing an oxygen transport membrane-based reforming system |
US9938146B2 (en) | 2015-12-28 | 2018-04-10 | Praxair Technology, Inc. | High aspect ratio catalytic reactor and catalyst inserts therefor |
EP3436185A1 (en) | 2016-04-01 | 2019-02-06 | Praxair Technology Inc. | Catalyst-containing oxygen transport membrane |
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WO2019212072A1 (en) * | 2018-05-02 | 2019-11-07 | 한국과학기술원 | Acetic acid production method using dry reforming process using carbon dioxide and system for same |
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EA007455B1 (en) * | 2002-05-20 | 2006-10-27 | Асетэкс (Кипр) Лимитед | Integrated process for making acetic acid and methanol |
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-
2004
- 2004-01-22 MX MXPA06007682A patent/MXPA06007682A/en active IP Right Grant
- 2004-01-22 KR KR1020107026583A patent/KR20100131528A/en not_active Application Discontinuation
- 2004-01-22 WO PCT/CY2004/000002 patent/WO2005070855A1/en active Application Filing
- 2004-01-22 AU AU2004314237A patent/AU2004314237B2/en not_active Ceased
- 2004-01-22 JP JP2006549841A patent/JP4633741B2/en not_active Expired - Fee Related
- 2004-01-22 RS YUP-2006/0418A patent/RS20060418A/en unknown
- 2004-01-22 US US10/596,955 patent/US7470811B2/en not_active Expired - Fee Related
- 2004-01-22 CA CA2551223A patent/CA2551223C/en not_active Expired - Fee Related
- 2004-01-22 PL PL380241A patent/PL209862B1/en unknown
- 2004-01-22 CN CN2004800405271A patent/CN1906145B/en not_active Expired - Fee Related
- 2004-01-22 EP EP04738452A patent/EP1708982A1/en not_active Withdrawn
- 2004-01-22 NZ NZ548230A patent/NZ548230A/en not_active IP Right Cessation
- 2004-01-22 BR BRPI0418477-7A patent/BRPI0418477B1/en not_active IP Right Cessation
- 2004-01-22 KR KR1020067016763A patent/KR101046116B1/en not_active IP Right Cessation
- 2004-01-22 UA UAA200609271A patent/UA85579C2/en unknown
-
2006
- 2006-07-18 ZA ZA2006/05928A patent/ZA200605928B/en unknown
- 2006-08-17 NO NO20063692A patent/NO20063692L/en not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
NZ548230A (en) | 2009-08-28 |
KR20070001962A (en) | 2007-01-04 |
NO20063692L (en) | 2006-10-19 |
US7470811B2 (en) | 2008-12-30 |
AU2004314237B2 (en) | 2011-03-10 |
AU2004314237A1 (en) | 2005-08-04 |
KR101046116B1 (en) | 2011-07-01 |
UA85579C2 (en) | 2009-02-10 |
CN1906145B (en) | 2010-09-29 |
ZA200605928B (en) | 2008-01-08 |
BRPI0418477B1 (en) | 2015-04-22 |
MXPA06007682A (en) | 2007-01-26 |
PL380241A1 (en) | 2007-01-08 |
CN1906145A (en) | 2007-01-31 |
CA2551223C (en) | 2011-05-03 |
JP4633741B2 (en) | 2011-02-16 |
BRPI0418477A (en) | 2007-06-19 |
KR20100131528A (en) | 2010-12-15 |
RS20060418A (en) | 2008-09-29 |
WO2005070855A1 (en) | 2005-08-04 |
EP1708982A1 (en) | 2006-10-11 |
PL209862B1 (en) | 2011-10-31 |
US20080039652A1 (en) | 2008-02-14 |
JP2007518745A (en) | 2007-07-12 |
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