BRPI0609525A2 - sìntese de hidrocarbono - Google Patents

sìntese de hidrocarbono Download PDF

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BRPI0609525A2
BRPI0609525A2 BRPI0609525-9A BRPI0609525A BRPI0609525A2 BR PI0609525 A2 BRPI0609525 A2 BR PI0609525A2 BR PI0609525 A BRPI0609525 A BR PI0609525A BR PI0609525 A2 BRPI0609525 A2 BR PI0609525A2
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hydrocarbons
zeolite
hydrocarbon
alkaline earth
earth metal
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Ivan M Lorkovic
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Grt Inc
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G50/00—Production of liquid hydrocarbon mixtures from lower carbon number hydrocarbons, e.g. by oligomerisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/26—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only halogen atoms as hetero-atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G27/00—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
    • C07C2521/10—Magnesium; Oxides or hydroxides thereof
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2529/00—Catalysts comprising molecular sieves
    • C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
    • C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • C07C2529/18—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the mordenite type
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2529/00—Catalysts comprising molecular sieves
    • C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
    • C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • C07C2529/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
    • C10G2400/02—Gasoline
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
    • C10G2400/20—C2-C4 olefins
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
    • C10G2400/22—Higher olefins
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
    • C10G2400/30—Aromatics
    • 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
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
    • 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S585/00—Chemistry of hydrocarbon compounds
    • Y10S585/929—Special chemical considerations
    • Y10S585/93—Process including synthesis of nonhydrocarbon intermediate
    • Y10S585/935—Halogen-containing
    • 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S585/00—Chemistry of hydrocarbon compounds
    • Y10S585/929—Special chemical considerations
    • Y10S585/943—Synthesis from methane or inorganic carbon source, e.g. coal

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  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

SìNTESE DE HIDROCARBONO. A presente invenção refere-se a um método de sintetização de hidrocarbonos a partir de hidrocarbonos menores que inclui as etapas de halogenação de hidrocarbono, oligomerização e neutralização de haleto de hidrogênio simultâneas e recuperação de produto, com um catalorreagente de metal-oxigênio usado para facilitar o acoplamento carbono-carbono. Tratamento com ar ou oxigênio libera halogênio e regenera o catalorreagente.

Description

Relatório Descritivo da Patente de Invenção para "SÍNTESE DE HIDROCARBONO".
Campo da Invenção
A presente invenção refere-se, em geral, à oligomerização dehidrocarbono, e, mais particularmente, a um método de fabricação de hidro-carbono usando catalorreagentes.
Antecedentes da Invenção
Os cientistas há muito tempo têm procurado por meios eficientespara converter metano e outros alcanos em hidrocarbonos superiores, inclu-indo olefinas leves e materiais da faixa de gasolina. Processos eficientespoderiam ser valiosos de várias maneiras, incluindo: facilitação da utilizaçãode gás natural encalhado remotamente localizado através de sua conversãoem combustíveis líquidos e matérias-primas mais facilmente transportáveis,e permitindo o uso de matérias-primas econômicas (metano e outros alcanosinferiores) para produtos finais freqüentemente feitos de alcanos superiores,incluindo etileno e propileno.
As Patentes U.S. Nss 6.486.368, 6.472.572, 6.465.699, 6.465.696e 6.462.243 descrevem processos para conversão de alcanos em olefinas,éteres e álcoois. Muitos dos processos descritos envolvem halogenação deum alcano, passagem dos produtos halogenados em um oxido de metal paracriar produtos e haleto de metal, recuperação do(s) produto(s) e regenera-ção do haleto de metal com oxigênio ou ar para dar oxido de metal e halo-gênio para reciclar para o processo. Não é descrita oligomerização de alca-no: acoplamento substancial do hidrocarbono de partida para se obter produ-to(s) de número de carbono maior.
Vários investigadores examinaram o uso de halogenação para aprodução de hidrocarbonos superiores a partir de metano. Patentes repre-sentativas incluem 4.513.092 (Chu), 4.769.504 (Noceti e Taylor), 5.087.786(Nubel) e 6.452.058 (Schweitzer). Conforme descrito na patente de Taylor:"Hidrocarbonos da faixa de ebulição de gasolina, ricos em aromáticos, [sãofeitos] a partir de alcanos inferiores, particularmente a partir de metano. Oprocesso é realizado em dois estágios. No primeiro, alcano é reagido comoxigênio e cloreto de hidrogênio em um catalisador de oxiidrocloração talcomo cloreto de cobre com proporções menores de cloreto de potássio ecloreto terroso-raro. Isto produz uma mistura gasosa intermediária contendoágua e alcanos clorados. Os alcanos clorados são contatados com um cata-lisador de aluminossilicato cristalino na forma promovida por hidrogênio oumetal para produzir hidrocarbonos da faixa de gasolina com uma proporçãoalta de aromáticos e uma porcentagem pequena de hidrocarbonos leves (C2-C4), bem como reforma do HCI. Os hidrocarbonos leves podem ser recicla-dos para processamento adicional no catalisador de oxiidrocloração". Todasessas técnicas para fabricação de alcanos superiores a partir de matérias-primas de C1 sofrem da desvantagem que a corrente de hidrocarbono deveser separada de uma corrente de ácido hidroálico aquosa, e a corrente ácidohidroálico deve ser reciclada.
A US 4.795.843 (Tomostu e outros) descreve um processo para oligomerização de halometanos para produtos incluindo etil benzeno, tolue-no e xilenos, usando catalisadores de sílica polimorfa ou silicalito. O proces-so não incorpora neutralização reativa de haleto de hidrogênio e parece so-frer de cinética lenta.
Em um processo para halogenação de hidrocarbonos, Chang ePerkins notaram quantidades traço de produtos de oligomerização na pre-sença de zeólitos na US 4.654.449. Os produtos de oligomerização estavampoucos em quantidade e geralmente halogenados.
A US 4.373.109 (Olah) descreve um processo para conversãode metanos heterossubstituídos, incluindo haletos de metila, através do con-tato de tais metanos com catalisadores de base de ácido bifuncionais emtemperaturas elevadas, entre 200 e 450°C, de preferência entre 250 e375°C, para produzir olefinas predominantemente inferiores, de preferênciaetileno e propileno. Os catalisadores de preferência são aqueles derivadosde haletos, oxialetos, óxidos, sulfetos ou oxissulfetos de metais de transiçãodos Grupos IV, V, VI, VIII da Tabela Periódica, tal como tântalo, nióbio, zir-cônio, tungstênio, titânio e cromo, depositados em óxidos e sulfetos ácidostal como alumina, sílica, zircônia ou sílica-alumina. Nem o uso de recupera-ção de halogênio baseado em oxido sólido nem a formação de álcoois ouéteres é descrito. Uma referência relatada é "Ylide chemistry 1. Bifuncionalacid-base-catalyzed conversion of heterosubstituted methanes into ethyleneand derived hydrocarbons. The onium-ylide mechanism of the C1->C2 con-version" de George A. Olah e outros (J. Am. Chem. Soe. 106, 2143 (1984)).
A US 3.894.107 (Butter e outros) descreve melhorias para umprocesso para condensação de hidrocarbonos halogenados usando catali-sadores de zeólito. Notavelmente ausente está qualquer discussão de neu-tralização de haleto de hidrogênio baseado em oxido sólido.
Kochi observou acoplamento redutivo de haletos de alquilaquando brometos de metal de transição são reagidos com reagentes deGrignard de peso molecular baixo em THH ou dietil éter {Bulletin of theChemical Society of Japan, v. 44 1971 pp. 3063-73). Química de fase líqui-da, no entanto, tipicamente sofre de tais desvantagens como a necessidade de solvente, corrosão e taxas menores de reação do que a química de gás.Ainda, tais processos consomem energia requerida para produzir o metal demagnésio necessário para os reagentes de Grignard energético e de redu-ção. Este não é o mesmo tipo de processo que o acoplamento desidroalo-genativo e neutralização de haleto de hidrogênio descritos aqui.
Sumário da Invenção
A presente invenção refere-se à necessidade de um modo efici-ente de converter metano e outros hidrocarbonos em hidrocarbonos superio-res. Em uma modalidade, um hidrocarbono tendo um número de carbono Cn,onde n > 2, é preparado permitindo que um hidrocarbono reagente tendo um número de carbono cm, onde m < n, reaja com um agente de halogenação,deste modo formando um hidrocarbono halogenado; permitindo que o hidro-carbono halogenado contate um catalorreagente de metal-oxigênio, destemodo formando um produto de hidrocarbono tendo um número de carbonoCn, onde n > 2; recuperação do produto de hidrocarbono; e regeneração docatalorreagente. Freqüentemente, uma mistura de hidrocarbonos é obtida,mas seleção cuidadosa do hidrocarbono reagente, agente de halogenação,catalorreagente de metal-oxigênio e condições de reação permite uma abor-dagem especialmente feita para formação de produto. Metano (isto é, gásnatural) bem como outros hidrocarbonos líquidos, por exemplo, C2 a C6 hi-drocarbonos, são previstos como matérias-primas preferidas. Mais geral-mente, a invenção compreende o uso de matérias-primas tendo números de carbono tão altos quanto C10. Observações de laboratório até agora têm fo-cado em oligomerização de metano e acoplamento de brometo de metila,com detecção de espécies C2-C10, incluindo alcanos, alcenos, hidrocarbonosramificados e compostos aromáticos.
Descrição Detalhada da Invenção
A presente invenção explora a verificação de que compostos demetal-oxigênio, tal com óxidos de metal mistos, zeólitos dopados (isto é,zeólitos dopados de metal alcalino-terroso), zeólitos impregnados com oxidode metal, etc, facilitam a oligomerização do hidrocarbono. De acordo comum aspecto da invenção, um hidrocarbono tendo um número de carbono Cn,onde n > 2, é formado através de (i) formação de um hidrocarbono haloge-nado ao permitir que um hidrocarbono reagente tendo um número de carbo-no Cm, onde m < n, reaja com um agente de halogenação; (ii) formação deum produto de hidrocarbono tendo um número de carbono Cn, onde n > 2,ao permitir que o hidrocarbono halogenado contate um catalorreagente demetal-oxigênio; (iii) recuperação do produto de hidrocarbono; e (iv) regene-ração do catalorreagente.
Mais geralmente, o método envolve as etapas de halogenação,oligomerização, recuperação de produto e regeneração de catalorreagente.Os produtos halogenados podem ser separados de hidrocarbono não-reagido (não-halogenado) ou antes ou após reação com o catalorreagentede metal-oxigênio. Neutralização de qualquer ácido hidroálico formado du-rante a síntese é vantajosamente realizada concomitantemente com aco-plamento de carbono-carbono e/ou regeneração de catalorreagente. De pre-ferência, o processo é um integrado e acontece, por exemplo, em um reator de zona, conforme descrito, por exemplo, na U.S. 6.525.230 (Grosso), cujosconteúdos em sua totalidade são aqui incorporados a título de referência.Deste modo, halogenação de metano ou outros hidrocarbonos acontecedentro de uma zona do reator, e é seguida por uma etapa de condensaçãoonde o ácido hidroálico liberado é absorvido dentro do mesmo material bi-funcional que catalisa condensação do hidrocarbono halogenado. Oligomeri-zação de hidrocarbono (definida como acoplamento carbono-carbono) acon-tece dentro desta zona do reator e dá produto de hidrocarbonos que, emgeral, terá números de carbono variando de C2 a C2o, e podem incluir alca-nos, alcenos, alcinas e/ou aromáticos. Tratamento com ar ou oxigênio liberahalogênio para uso em etapas de halogenação subseqüentes, e regenera omaterial catalorreagente para condensação ou metátese subseqüente. Van- tajosamente, a necessidade de reciclar/recuperar ácido hidroálico aquoso,corrosivo, é evitada porque regeneração e recuperação acontecem in situ.
Síntese de hidrocarbono superior começa com uma matéria-prima de hidrocarbono: um ou mais reagente de hidrocarbono, cada um ten-do, independentemente, um número de carbono Cm, onde m < n, Cn sendo onúmero de carbono do hidrocarbono(s) alvo. Exemplos não-limitantes dehidrocarbonos reagentes incluem metano, etano, propano, etc, com gás na-tural (predominantemente metano, mas freqüentemente incluindo quantida-des pequenas de C2 e espécies superiores) sendo preferido. Em geral, ohidrocarbono de partida tem um número de carbono entre 1 e 10. Misturasde hidrocarbonos podem ser também usadas.
Os hidrocarbonos reagentes são deixados reagir com um agentede halogenação. Exemplos não-limitantes incluem halogênio molecular (porexemplo, bromo, cloro, etc), haletos de alquila (por exemplo, dibromometa-no, bromofórmio, tetrabrometo de carbono) e haletos condensados, tal comobrometos de metal, que podem estar presentes como um material sólido,líquido, apoiado ou não-apoiado.
Halogênios moleculares são preferidos, com bromo (Br2) sendopreferido. Bromo é um líquido em temperatura ambiente, menos reativo doque cloro e flúor, e fácil de manusear. Bromo também tem energética favo-rável.
O potencial de redução de bromo em brometo é 1,07 V vs. NHE,enquanto que o oxigênio para água é 1,23 V. Uma faixa ampla de brometosde metal pode liberar bromo quando do tratamento com oxigênio. Ao mesmotempo, brominação de alcano e subseqüente acoplamento de brometo dealquila e neutralização com HBr são apenas levemente exotérmicos, masespontâneos o suficiente para irem ao término. Água e hidrocarbonos aco- piados são os únicos produtos fluidos. O mesmo não é verdadeiro com clorocomo mediador, para o qual HCI é um componente principal da corrente deproduto. Produção de cloreto de hidrogênio requer separação, secagem ereciclagem, o que é caro dispendioso. Resumindo, a termoquímica de oxida-ção parcial de alcano mediada por brometo de metal é bem-adequada para operação de fábrica eficiente e econômica.
Halogenação do hidrocarbono reagente pode acontecer de vá-rias maneiras, dependendo em parte do(s) produto(s) desejado e em parteda alimentação. Em uma modalidade, um alcano é halogenado com halogê-nio molecular usando calor, luz ou outra radiação eletromagnética para dirigir a reação, com calor sendo preferido. Há algum benefício em ter todas asetapas - halogenação, oligomerização e regeneração (descritas abaixo) -acontecendo aproximadamente na mesma temperatura. Para processos demetal em olefina (MTO) e metanol em gasolina (MTG), temperaturas de apartir de 375 a 450°C são utilizadas, com a faixa sendo importante, se não crítica. Para o processo de acoplamento de carbono-carbono descrito aqui,uma faixa de temperatura ideal, onde todas as etapas acontecem aproxima-damente na mesma temperatura, é 450 a 550°C.
No entanto, etapas de reação individuais seriam realizadas emtemperaturas acima ou abaixo desta faixa. Na verdade, rendimentos de ga-solina são melhores em temperaturas de reação menores e, em alguns dosexemplos abaixo, a reação de brometo de metila com um zeólito dopadocom metal alcalino-terroso é realizada em uma temperatura de a partir de225 a 350°C e uma pressão de a partir de 100 a 500 KPa (1 a 5 bar). Paraum processo completamente integrado, no entanto, a engenharia favorece a realização de todas as três reações em uma temperatura similar.
Halogenação de preferência acontece em uma pressão entre0,01 e 202,65MPa (0,1 e 200 atm) para a subseqüente etapa de carbono-carbono. Pressão baixa favorece menos acoplamento carbono-carbono (istoé, um peso molecular médio menor de produto), enquanto pressão alta favo-rece acoplamento maior. Processos para olefinas leves são prováveis derealizar nos mesmos 412 a 1377 KPa (abs) (60 a 200 psia) que processosde metal em olefina (MTO) são realizados, embora pressões mais altas pos-sam ser alternativamente utilizadas. Para produção de moléculas de faixa degasolina, pressões em torno de 2411 KPa (abs) (350 psia), conforme usadoem processos de metal em gasolina (MTG), são pretendidas. Como umaquestão prática, realização abaixo da atmosférica (mais conservativamente,abaixo de 13,7 KPa (abs)(2 psia)) ou acima de 689,5 KPa (100 atm) é im-provável.
Quando halogênio molecular é usado como o agente de haloge-nação, a halogenação é idealmente realizada em uma razão de alca-no:halogênio entre 1:10 e cerca de 100:1, em um volume em base de volu- me. Em razões de alcano:halogênio de menos do que 1:10 (isto é, mais ha-logênio), hidrocarbonos multialogenados serão formados, tipicamente levan-do à oxidação completa (isto é, CO2) quando do contato subseqüente com ocatalorreagente de metal-oxigênio. Em razões de alcano-halogênio maioresdo que 100:1, a conversão do hidrocarbono halogenado será também muitobaixa, talvez 1% ou menos, e é quase impossível imaginar um processo e-conômico em tais níveis de conversão. (30-60% de conversão são limitesinferiores mais prováveis).
Alteração da razão de halogênio em alcano ou outras matérias-primas de hidrocarbono pode ter um impacto acentuado sobre a distribuiçãode produto. Por exemplo, uma pessoa pode escolher controlar o grau de ha-logenação a fim de reduzir a formação aromática na produção de olefinas oucombustíveis inferiores. Um segundo exemplo é minimizaçao da formaçãode metano altamente halogenado a fim de reduzir a formação de alcinas.
Uma característica-chave da invenção é o uso de um catalorrea-gente de metal-oxigênio, que facilita o acoplamento carbono-carbono, isto é,oligomerização de hidrocarbono. O termo "catalorreagente de metal-oxigênio" é usado aqui para se referir a um material de catalorreagente con-tendo ambos metal e oxigênio. Embora não limitado pela teoria, acredita-seque o material catalise acoplamento carbono-carbono através de haleto dehidrogênio (por exemplo, HBr) eliminação e inserção de alquilideno em C-Hionicamente ativado e possivelmente ligações C-C. O catalorreagente tam-bém age como um agente de liberação e seqüestro de halogênio, e oferecea possibilidade de obtenção de uma distribuição de produto de acoplamentoajustável, incluindo a habilidade em produzir oxigenatos se desejado, en-quanto simultaneamente aprisionamento e recuperando halogênio, emitindoapenas água como um subproduto. Tratamento com ar ou oxigênio regenerao catalorreagente.
Exemplos não-limitantes de catalorreagentes de metal-oxigênioincluem zeólitos, zeólitos dopados, óxidos de metal, óxidos de metal mistos,zeólitos impregnados com oxido de metal e materiais similares, bem comomisturas de tais materiais. Exemplos não-limitantes de dopantes incluemmetais alcalino-terrosos, tal como cálcio e magnésio, e seus óxidos e/ou hi-dróxidos.
Zeólitos estão disponíveis de uma variedade de fontes, incluindoZeolyst International (Valley Forge, PA). Exemplos específicos incluem ZSM-5 dopado e mordenita dopada (onde, por exemplo, cálcio e/ou magnésio sãoos dopantes).
Mudança das propriedades de zeólito ou componente de zeólitode um composto de zeólito/óxido de metal é também esperada para mudardistribuição de produto. Tamanho de poro e acidez são particularmente es-perados ser importantes. Acidez pode ser usada para controlar o compri-mento de cadeia e funcionalidade, e tamanho de poro pode controlar o com-primento de cadeia e funcionalidade. Zeólitos de tamanho de poro particularpodem seletivamente produzir benzeno, tolueno, para-xileno, orto-xileno,meta-xileno, xilenos misturados, etil benzeno, estireno, alquil benzeno linearou outros produtos aromáticos. O uso de tamanho de poro não é limitado aprodutos aromáticos.
Em uma modalidade da invenção, um composto de oxido de me-tal/zeólito é preparado através de mistura de um zeólito com um nitrato demetal (por exemplo, um oxido de metal alcalino-terroso, tal como nitrato decálcio) ou suas espécies hidratadas, é então calcinação desta mistura paraliberar óxidos de nitrogênio e reter o zeólito impregnado com oxido de metal.
Após oligomerização, o catalorreagente de metal-oxigênio é re-generado através de tratamento com ar ou oxigênio, tipicamente em umatemperatura de a partir de 200 a 900°C. Isto converte espécie de haleto demetal em espécie de metal-oxigênio.
Várias variáveis, incluindo composições de alimentação, locali-zação de alimentação no reator, temperatura, pressão, composição do oxidode metal e tempo de residência no reator podem alterar a distribuição doproduto. Produção de alcanos, olefinas e aromáticos a partir do metano foidetectada e confirmada. Também esperada é a habilidade em produzir alca-nos e olefinas de ramificação particular (incluindo álcoois monometílicos ra-mificados), álcoois, dióis, éteres, hidrocarbonos halogenados, aromáticosincluindo benzeno, estireno, etil benzeno, tolueno, xilenos e alquil benzenoslineares e hidrocarbonos adequados para combustíveis tal como gasolina,diesel e combustível para avião.
Controle da composição de alimentação pode controlar a distri-buição de produção. Primeiro, haleto de hidrogênio produzido na halogena-ção pode ser neutralizado (para formar água ou álcool) com o mesmo com-posto de metal-oxigênio produzindo o(s) produto(s) de hidrocarbono, ou comum composto de metal-oxigênio separado em um reator distinto. Mudançado local de neutralização de haleto de hidrogênio pode mudar a distribuiçãode produto, incluindo funcionalidade, comprimento de cadeia e ramificação.
Por exemplo, neutralização e formação de produto concorrentes podem seresperadas para direcionar a produção de álcoois, que pode ou não sofrerreações adicionais tal como acoplamento ou desidratação. Segundo, adiçãode água à alimentação pode mudar a distribuição de produto. Em particular,a adição de água pode favorecer produtos de álcool. A adição de água podetambém controlar o grau e tipo de ramificação e comprimento de cadeia.Terceiro, adição de hidrogênio pode alterar a distribuição de produto. Hidro-gênio pode aumentar alcanos ao custo de outras funcionalidades, algo parti-cularmente útil para produção de combustíveis. Hidrogênio pode tambémreduzir coque e ajuda a controlar o comprimento e ramificação de cadeia.
Será também compreendido que oligomerização de carbono-carbono pode acontecer através de vários cursos. Até matérias-primas dehidrocarbono sozinho podem dar mais de um produto. Por outro lado, emuma modalidade da invenção, halogenação controlada é usada para produ-zir predominantemente um isômero em favor de outro (por exemplo, forma-ção seletiva de 1 -buteno ou 2-buteno). Matérias-primas mistas, tal como gásnatural bruto, podem dar origem à oligomerização de hidrocarbonos múlti-plos halogenados (por exemplo, haleto de etila, dialoetano, haleto de metila,dialeto de metila, haleto de propila, dialeto de propila, etc). Na verdade, emuma modalidade da invenção, um haleto de alquila é propositadamente in-troduzido para criar produtos ramificados desejados. Um exemplo seria oli-gomerização de haleto de metila (a partir de metano) com haleto de metilaou um haleto de alquila superior para produzir, seletivamente, ramificação demetila, etila, propila, isopropila ou butila terciária (ou outra). Um outro exem-plo seria a síntese de estireno a partir de haleto de etila, haleto de metila edialometano.
Em uma modalidade da invenção, a reação de hidrocarbono ha-logenado com um catalorreagente de metal-oxigênio acontece em um leitofluidizado. Alternativamente, um leito fixo é empregado. Haletos de alquiladiferentes podem ser introduzidos em locais diferentes no reator. Um exem-plo é a introdução de haletos de metal em um local no reator para produzirbenzeno, ao qual haletos de etila são adicionados, produzindo estireno ouetil benzeno. Um outro exemplo é a introdução de haletos de metila em umlocal no reator para produzir benzeno, ao qual haletos de alquila são adicio-nados, produzindo alquil benzeno linear.
Separação de produto é realizada através de qualquer métodoadequado. Exemplos não-limitantes incluem destilação, absorção e extra-ção. Produto(s) pode(m) ser recuperado(s) a partir do sólido através de re-moção {stripping) com vapor, dióxido de carbono ou outros meios.
O que segue são exemplos não-limitantes da invenção.Exemplo 1
Composto de Oxido de Metal/Zeólito MZ1 foi preparado comosegue: Uma mistura sólida de um zeólito tipo ZSM-5 (Zeolyst CBV 8014, ra-zão de Si/Al = 80:1, 10 g, 170 mmols de Si02) e monoidrato de CaN03 (9 g = 34 mmols de Ca) foi preparado e água foi adicionada até umidade incipiente.Após dissolução e agitação de CaN03, a pasta fluida foi seca e calcinada emseqüência a 115°C (da noite para o dia) e 500°C (da noite para o dia), res-pectivamente, em ar.
Exemplo 2
Metano a 103,4 KPa (abs) (15 psia) foi borbulhado através debromo a 1 °C em uma taxa de 5 cm3/min. A corrente de bromo e metano resul-tante (1:10 em mol) foi passada por um reator de brominação de diâmetro pe-queno a 450°C (1000 h"1 e mistura de CH4-xBrx (x = 0, 1,2, 3) passada emum reator contendo 5 g de composto de oxido de metal/zeólito MZI (400 C). Acorrente de saída a partir do segundo reator não continha quaisquer produtosbrominados. Com base no metano consumido no reator de brominação, 10%de etileno, 31% de propileno, 3% de propano e 21% de butanos/butenos fo-ram detectados; 65% no geral. Quantidades traço de espécies C6 foram tam-bém detectadas. Após reação por 5 horas, durante o que a saída de correntenão mudou da distribuição acima descrita, a corrente de metano foi desconti-nuada e o reator foi purgado com hélio a 5 cm3/min por 10 minutos. Após pur-ga de He, um fluxo de O2 (2 cm3/min) no segundo reator foi iniciado a 525°Cpara regenerar o oxido de metal a partir do brometo de metal do compostoparcialmente usado. Inicialmente apenas água e CO2 foram observados comoprodutos, mas abruptamente os teores da corrente mudaram para Br2 e 02não-reagido. Após 1 hora, a purga de 02 foi descontinuada e o reator foi no-vamente purgado com hélio. O filtro cáustico usado durante a regeneração foitestado quanto a C03"2 e 1,0 mmol foi encontrado, representando 24% docarbono convertido. O restante do carbono foi verificado ser aromáticos volá-teis ferventes superiores (principalmente tolueno, xilenos e mesitilenos). Umsegundo ciclo de condensação de bromometanos conforme acima descrito foiiniciado a 400°C e a distribuição de produto foi verificada ser idêntica à primei-ra rodada. Mais três ciclos de condensação/neutralização/regeneração produ-ziram o mesmo resultado de hidrocarbonos superiores.Exemplo 3
Uma mordenita dopada (Zeolyst CBV 21 A, dopada com ambosCa e Mg) (5 g) foi preparada de acordo com o Exemplo 1 e usada como ocatalorreagente em uma síntese de hidrocarbono substancialmente similaràquela descrita acima no Exemplo 2. O resultado de produto era 30% deetileno, 5% de etano, 10% de propileno, 3% de propano, 5% de buta-nos/butenos. Rodadas múltiplas e regeneração de catalorreagente estabele-ceram reprodutibilidade.
Exemplos 4-15
Um zeólito do tipo ZSM-5 (Zeolyst CBV 28014, tendo uma razãode 280:1 de Si:AI) da Zeolyst Corp. foi dopado com cálcio de acordo com oprocedimento descrito no Exemplo 1, para uma razão de 4:1 de Ca.Si. Umtubo de reação de vidro (15,24 cm (6 pol) de comprimento; 4 mm de diâme-tro interno) foi carregado com 1,427 g do zeólito dopado com cálcio, moídogrosseiramente, e uma corrente de brometo de metila (4,5 mmols) foi deixa-da fluir no tubo. Após conversão do brometo de metila, o sólido foi regenera-do através de tratamento com 02 (2 sccm, 100 KPa (1 bar)) a 520°C por 3horas, e Br2 desenvolvido por recuperado. A reação de acoplamento debrometo de metila foi realizada em uma faixa de pressões, temperatura etaxas de fluxo usando o mesmo sólido e a mesma quantidade de brometo demetila por rodada. Produtos e nenhum brometo de metila não-reagido saí-ram pela extremidade oposta do tubo de reação e foram analisados atravésde um ou mais de GC, GC/MS e RMN. Devido a razões de isótopo e pa-drões de fragmentação inequívocos GC/MS é particularmente útil como umdiagnóstico de teor de bromoidrocarbono (que, tipicamente, é zero).
A Tabela 1 sumariza as distribuições de produto de hidrocarbono(também referidas como "seletividade" (sei), expressas como uma porcentagem),conversão percentual de CH3Br e parâmetros de reação T, P e t (espaço tempo),onde t foi calculado de acordo com a equação: t = volume do reator/taxa de fluxode entrada. Distribuições de produto aromático estão sublinhadas.Tabela 1. Exemplos 4-15: acoplamento de CH3Br em ZSM-5 dopado com
Ca: Parâmetros e produtos de reação (1â parte)
<table>table see original document page 14</column></row><table>
Conversões:
1bar-> 100 KPa 3 bar -> 300 KPa 5 bar -> 500 KPaConforme visto na Tabela 1, um zeólito dopado com metal alca-lino-terroso facilitou a conversão de alcano brominado (CH3Br) em vários hidrocarbonos diferentes, incluindo alcanos lineares e ramificados, olefinas e compostos aromáticos. Água foi também produzida, bem como subproduto de neutralização de HBr. Análise GC de produtos mostrou altas conversões de brometo de metila (com conversões menores acontecendo em temperaturas baixas, e conversões maiores acontecendo em temperaturas altas), e medições de pH mostraram neutralização completa de HBr formado na reação.
Em geral, a porcentagem de C5 e hidrocarbonos superiores produzidos para uma dada rodada excedeu 70%, e a porcentagem de C6 e hidrocarbonos superiores produzidos excedeu 50%. Compostos aromáticos detectados incluem tolueno (C7), xilenos e etilbenzeno (C8), mesitilenos e etilmetilbenzeno (C9) e hidrocarbonos superiores (por exemplo, Cio). Em algumas rodadas, uma quantidade pequena de benzeno foi detectada.
Embora não limitado pela teoria, o acoplamento carbono-carbono parece acontecer em dois estágios, similar ao que é observado com a formação de hidrocarbono a partir de acoplamento de metanol. Em um primeiro estágio, rápido, olefinas parecem se formar, acoplar e então quebrar. Isto parece ser seguido por um segundo estágio, mais lento, dando produtos aromáticos e parafinas após longa exposição ao catalisador e temperaturas maiores.
Foi observado que catalorreagente sólido recém-preparado não dá a distribuição de produção de "estado uniforme" obtida após 1 ciclo (e repetida por vários ciclos adicionais) de acoplamento/seqüestro de bromo, seguido por reoxigenação sólida liberação de bromo. Isto é, distribuições de produto de "primeira rodada" são diferentes das distribuições vistas usando catalorreagente sólido reciclado. Exemplos 16-18
Para demonstrar que hidrocarbonos mais leves podem ser reciclados no reator de acoplamento, primeiro propileno (4,5 mmols) e então uma mistura de CH3Br e propileno (3:1 v/v ou 3,3 mmols:1,1 mmol) foramutilizados como uma alimentação em um tubo de reação de vidro configurado conforme descrito nos Exemplos 4-15. A distribuição de produto foi comparada com aquela obtida usando CH3Br (4,5 nmmols) sozinho. Os resultados são apresentados na Tabela 2. As distribuições de produto aromático são sublinhadas.
Tabela 2. Exemplos 16-18: Produtos de reação para propileno (Ex. 16); 3:1 de CH3Br:propileno (Ex. 17); e CH3Br sozinho (Ex. 18) em ZSM-5 dopado com Ca. (1-parte)
<table>table see original document page 16</column></row><table>
Tabela 2. (2â parte) <table>table see original document page 16</column></row><table>
Conversões
3 bar -> 300 KPa5bar-»500KPa
A Tabela 2 mostra que olefinas leves menos desejáveis (a partir do ponto de vista de produção de gasolina) podem ser recicladas na corrente de alimentação para incorporação a produtos mais pesados. O fato de que a distribuição de produto para uma alimentação de propileno é similar àquela para MeBr e MeBr/propileno 1:1 (base C:C) mostra que a reciclagemde olefinas leves vai melhorar o rendimento geral de produtos de gasolina.
A invenção foi descrita através de referência a vários exemplos e modalidades preferidas, mas não é limitada a eles. Outras modificações e substituições podem ser feitas sem se afastar do escopo da invenção. Porexemplo, os processos de oligomerização descritos aqui também pretendem compreender halogenação de matérias-primas de olefina usando um haleto de hidrogênio (por exemplo, HBr) ou halogênio molecular; halogenação de acetilenos (alcinas) usando haleto de hidrogênio ou halogênio molecular; halogenação de álcoois ou éteres usando haleto de hidrogênio ou halogênio molecular; e halogenação de alcanos usando halogênio molecular e um catalisador que controla a halogenação. Especificamente, o catalisador pode controlar um ou ambos o grau de halogenação (número de halogênios por molécula) e a posição de halogenação (por exemplo, halogenação terminal vs. Interna para um alceno de cadeia longa). Outras modificações podem ser feitas também. A invenção é limitada apenas pelas reivindicações apensas e seus equivalentes.

Claims (20)

1. Método de fabricação de uma pluralidade de hidrocarbonos compreendendo:permitir que brometo de metila contate um zeólito dopado com um metal alcalino-terroso em temperatura e pressão suficientes para dar uma pluralidade de hidrocarbonos.
2. Método de acordo com a reivindicação 1, em que o metal alcalino-terroso é selecionado do grupo consistindo em cálcio, magnésioe suas misturas.
3. Método de acordo com a reivindicação 1, em que o zeólito tem uma razão de AI:Si de a partir de cerca de 80:1 a cerca de 280:1.
4. Método de acordo com a reivindicação 1, em que o zeólito tem uma razão de AI:Si de cerca de 80:1.
5. Método de acordo com a reivindicação 1, em que o zeólito tem uma razão de AI:Si de cerca de 280:1.
6. Método de acordo com a reivindicação 1, em que o zeólito dopado com um metal alcalino-terroso tem uma razão de metal alcalino-terroso:silício de cerca de 4:1.
7. Método de acordo com a reivindicação 1, em que a pluralidade de hidrocarbonos inclui pelo menos um hidrocarbono aromático.
8. Método de acordo com a reivindicação 7, em que pelo menos um hidrocarbono aromático compreende pelo menos um hidrocarbono selecionado do grupo consistindo em benzeno, tolueno, xileno, etilbenzeno, me-sitileno e etilmetilbenzeno.
9. Método de acordo com a reivindicação 1, em que a pluralidade de hidrocarbonos inclui pelo menos um alcano ramificado.
10. Método de acordo com a reivindicação 1, em que a pluralidade de hidrocarbonos inclui pelo menos uma olefina.
11. Método de acordo com a reivindicação 1, em que a pluralidade de hidrocarbonos inclui pelo menos um alcano, pelo menos uma olefina e pelo menos um hidrocarbono aromático.
12. Método de acordo com a reivindicação 1, em que a plurali-dade de hidrocarbonos compreende uma mistura de hidrocarbonos de grau de gasolina.
13. Método de acordo com a reivindicação 1, compreendendo ainda permitir que quaisquer hidrocarbonos Ci a Caque são formados contatar um zeólito dopado com um metal alcalino-terroso para formar um ou mais hidrocarbonos C4 ou superiores.
14. Método de acordo com a reivindicação 1, em que o brometo de metila é formado através de brominação de metanol.
15. Método de acordo com a reivindicação 14, em que Br2 é usado para brominar metano.
16. Método de fabricação de uma pluralidade de hidrocarbonos compreendendo:permitir que brometo de metila contate um zeólito dopado com um metal alcalino-terroso em temperatura e pressão suficientes para dar uma pluralidade de hidrocarbonos, pelo menos 50% dos quais são hidrocarbonos C6 ou superiores.
17. Método de fabricação de uma pluralidade de hidrocarbonos compreendendo:permitir que brometo de metila contate um zeólito dopado com um metal alcalino-terroso em temperatura e pressão suficientes para dar uma pluralidade de hidrocarbonos, pelo menos 70% dos quais são hidrocarbonos C5 ou superiores.
18. Método de fabricação de uma pluralidade de hidrocarbonos compreendendo:permitir que brometo de metila contate um zeólito dopado com um metal alcalino-terroso em temperatura e pressão suficientes para dar uma pluralidade de hidrocarbonos, pelo menos 50% dos quais são hidrocarbonos C6ou superiores e pelo menos 70% dos quais são hidrocarbonos C5 ou superiores.
19. Método de acordo com a reivindicação 18, em que a temperatura é 225°C a 350°C e a pressão é 100 a 500 KPa (1 a 5 bar).
20. Método de acordo com a reivindicação 18, em que o zeólito dopado é um zeólito tipo ZSM-5 dopado com cálcio para uma razão de 4:1 de Ca:Si.
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