# US 9,517,984 B2 · Conversion of 2,3-butanediol to 2-butanol, olefins and fuels > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,517,984 B2 - Document ID: US9517984B2 - Status: Granted - Kind: B2 - Application number: 14/678,729 - Filed: 2015-04-03 - Published: 2015-10-08 - Granted: 2016-12-13 - Earliest claimed: 2014-04-04 - Assignees: Battelle Memorial Institute - Applicants: Battelle Memorial Institute - Inventors: Michael A. Lilga; Guo-Shuh Lee; Suh-Jane Lee - Web page: https://patentgrep.com/patent/US9517984B2 ## CPC - C07C 29/145: with hydrogen or hydrogen-containing gases - C07C 29/60: by elimination of -OH groups, e.g. by dehydration (C07C29/34 takes precedence) - C07C 45/29: of hydroxy groups - C07C 45/52: by dehydration and rearrangement involving two hydroxy groups in the same molecule - C10G 3/44: {characterised by the catalyst used} - C10G 45/00: Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds - C10L 1/04: essentially based on blends of hydrocarbons - C07C 29/172: {with the obtention of a fully saturated alcohol} - C10G 2400/30: Aromatics - Y02P 30/20: using bio-feedstock - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - C10G: CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION (cracking to hydrogen or synthesis gas C01B; cracking or pyrolysis of hydrocarbon gases to individual hydrocarbons or mixtures thereof of definite or specified constitution C07C; cracking to cokes C10B); RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES - C10L: FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS - Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS ## Abstract Embodiments of an integrated method for step-wise conversion of 2,3-butanediol to 2-butanol, and optionally to hydrocarbons, are disclosed. The method includes providing an acidic catalyst, exposing a composition comprising aqueous 2,3-butanediol to the acidic catalyst to produce an intermediate composition comprising methyl ethyl ketone, providing a hydrogenation catalyst that is spatially separated from the acidic catalyst, and subsequently exposing the intermediate composition to the hydrogenation catalyst to produce a composition comprising 2-butanol. The method may further include subsequently exposing the composition comprising 2-butanol to a deoxygenation catalyst, and deoxygenating the 2-butanol to form hydrocarbons. In some embodiments, the hydrocarbons comprise olefins, such as butenes, and the method may further include subsequently exposing the hydrocarbons to a hydrogenation catalyst to form saturated hydrocarbons. ## Claims ### Claim 1 A method, comprising: converting 2,3-butanediol to 2-butanol by exposing a composition comprising aqueous 2,3-butanediol to an acidic catalyst to produce an intermediate composition comprising methyl ethyl ketone, and subsequently exposing the intermediate composition to a hydrogenation catalyst to produce a composition comprising 2-butanol, wherein the hydrogenation catalyst is spatially separated from the acidic catalyst. ### Claim 2 (depends on 1) The method of claim 1, wherein the composition comprises 50-95 wt % 2,3-butanediol. ### Claim 3 (depends on 1) The method of claim 1, wherein the acidic catalyst is a solid acid catalyst. ### Claim 4 (depends on 1) The method of claim 1, wherein the acidic catalyst comprises an H-ZSM-5 zeolite, an amorphous silicoaluminate, alumina, niobic acid, or a combination thereof. ### Claim 5 (depends on 1) The method of claim 1, wherein the composition is exposed to the acidic catalyst at a temperature within a range of 150° C. to 500° C. and/or at a pressure within a range of 10 psig to 1200 psig. ### Claim 6 (depends on 1) The method of claim 1, wherein the hydrogenation catalyst comprises Ru/C, Raney nickel, Re/Ni/C, Pt/C, or a combination thereof. ### Claim 7 (depends on 1) The method of claim 1, wherein the intermediate composition is exposed to the hydrogenation catalyst at a temperature within a range of 60° C. to 300° C. and/or a pressure within a range of 10 psig to 1200 psig. ### Claim 8 (depends on 1) The method of claim 1, further comprising: subsequently exposing the composition comprising 2-butanol to a deoxygenation catalyst; and deoxygenating the 2-butanol to produce hydrocarbons. ### Claim 9 (depends on 8) The method of claim 8, wherein the deoxygenation catalyst comprises a solid acid catalyst. ### Claim 10 (depends on 8) The method of claim 8, wherein: the 2-butanol is exposed to the deoxygenation catalyst at a temperature within a range of 200° C. to 275° C., and the hydrocarbons comprise unbranched C4-C12 olefins, branched C4-C12 olefins, or a combination thereof; the 2-butanol is exposed to the deoxygenation catalyst at a temperature between 275° C. and 350° C., and the hydrocarbons comprise a mixture of aromatics, unbranched olefins, and branched olefins; or the 2-butanol is exposed to the deoxygenation catalyst at a temperature within a range of 350° C. to 500° C., and the hydrocarbons comprise at least 40% aromatic hydrocarbons. ### Claim 11 (depends on 8) The method of claim 8, wherein the hydrocarbons comprise olefins, the method further comprising exposing the olefins to a subsequent hydrogenation catalyst to form saturated hydrocarbons. ### Claim 12 (depends on 1) The method of claim 1, wherein the acidic catalyst is disposed within a first column, the hydrogenation catalyst is disposed within a second column, and the method further comprises: flowing the aqueous composition comprising 2,3-butanediol through the first column to produce the intermediate composition; and concurrently flowing the intermediate composition and hydrogen through the second column to produce the composition comprising 2-butanol. ### Claim 13 (depends on 12) The method of claim 12, further comprising concurrently flowing hydrogen through the first column with the composition. ### Claim 14 (depends on 12) The method of claim 12, wherein a deoxygenation catalyst is disposed within a third column, and the method further comprises flowing the composition comprising 2-butanol through the third column to produce hydrocarbons. ### Claim 15 (depends on 14) The method of claim 14, wherein the hydrocarbons comprise olefins, a hydrogenation catalyst is disposed within a fourth column, and the method further comprises flowing the hydrocarbons through the fourth column to produce saturated hydrocarbons. ### Claim 16 A method, comprising: converting 2,3-butanediol to hydrocarbons by flowing an aqueous composition comprising 50-95 wt % 2,3-butanediol through an acidic catalyst bed disposed in a first column to produce an intermediate composition comprising methyl ethyl ketone, flowing the intermediate composition and hydrogen concurrently through a hydrogenation catalyst bed disposed in a second column to produce a composition comprising 2-butanol, and flowing the composition comprising 2-butanol through a deoxygenation catalyst bed disposed in a third column to produce hydrocarbons. ### Claim 17 (depends on 16) The method of claim 16, wherein the hydrocarbons comprise olefins, the method further comprising flowing the hydrocarbons through a subsequent hydrogenation catalyst disposed in a fourth column to produce saturated hydrocarbons. ### Claim 18 A method, comprising: concurrently flowing hydrogen and an aqueous composition comprising 50-95 wt % 2,3-butanediol through a column including an acidic catalyst bed and a hydrogenation catalyst bed positioned distal to the acidic catalyst bed to produce a composition comprising 2-butanol. ### Claim 19 (depends on 18) The method of claim 18, wherein the column further includes a deoxygenation catalyst bed positioned distal to the hydrogenation catalyst bed, and flowing the composition comprising aqueous 2,3-butanediol through the column produces a composition comprising hydrocarbons. ### Claim 20 (depends on 19) The method of claim 19, wherein the column further includes a subsequent hydrogenation catalyst bed positioned distal to the deoxygenation catalyst bed, and flowing the composition comprising aqueous 2,3-butanediol through the column produces a composition comprising saturated hydrocarbons.