Evonik Operations GmbH v. Air Products Chemicals Inc

I. Executive Summary and Procedural Information

• Parties & Counsel:
  • Plaintiff: Evonik Operations GmbH (Germany) and Evonik Corporation (Alabama)
  • Defendant: Air Products and Chemicals, Inc. (Delaware) and Greenlane Biogas US Corp. (Delaware)
  • Plaintiff's Counsel: Tarter Krinsky & Drogin LLP
• Case Identification: 1:22-cv-01543, D. Del., 09/06/2023
• Venue Allegations: Venue is asserted in the District of Delaware on the basis that both Defendants are Delaware corporations and are subject to personal jurisdiction in the district.
• Core Dispute: Plaintiff alleges that Defendant Greenlane's biogas upgrading systems, which incorporate membrane components from Defendant Air Products, infringe two patents related to multi-stage membrane processes for gas separation.
• Technical Context: The technology concerns membrane-based systems used to separate gas mixtures, particularly for upgrading raw biogas by removing carbon dioxide to produce high-purity biomethane, also known as renewable natural gas (RNG).
• Key Procedural History: The complaint notes that U.S. Patent No. 8,999,038 survived an ex parte reexamination, with a certificate confirming its validity issued in March 2022. The complaint also alleges that Defendant Air Products filed an Opposition against the European counterpart of the '038 patent in 2017, a fact that may be used to support allegations of pre-suit knowledge and willful infringement.

Case Timeline

Date	Event
2010-07-01	Priority Date for U.S. Patent No. 8,999,038
2014-12-29	Priority Date for U.S. Patent No. 10,471,380
2015-04-07	Issue Date of U.S. Patent No. 8,999,038
2017-11-21	Alleged date of Air Products' Opposition to European counterpart of '038 Patent
2019-11-12	Issue Date of U.S. Patent No. 10,471,380
2022-03-29	Reexamination Certificate issued for U.S. Patent No. 8,999,038
2023-09-06	Amended Complaint Filed

II. Technology and Patent(s)-in-Suit Analysis

U.S. Patent No. 8,999,038 - "Process for separation of gases"

• Patent Identification: U.S. Patent No. 8,999,038 ("the Ungerank Patent"), titled "Process for separation of gases," issued on April 7, 2015.

The Invention Explained

• Problem Addressed: The patent describes a problem in prior art gas separation systems where achieving high purity for both the retained gas (retentate) and the permeated gas was difficult without costly and complex recompression steps, leading to energy inefficiency and loss of valuable product (e.g., methane slippage) Compl. ¶18 '038 Patent, col. 2:59-65
• The Patented Solution: The invention is a three-stage membrane separation apparatus and process (feed stage, retentate stage, permeate stage) designed to overcome this issue. The configuration recycles two internal streams-the permeate from the second stage and the retentate from the third stage-back to the initial feed stream. The patent specifies that this process is configured such that the total recycled gas volume is less than 60% of the crude gas stream and avoids recompressing the permeate from the first stage, thereby enabling the simultaneous production of high-purity retentate and permeate products efficiently '038 Patent, abstract '038 Patent, Fig. 11
• Technical Importance: This process claims to offer an energy-optimized method to achieve high yields of two purified gas products, a key consideration for the economic viability of applications like upgrading biogas to pipeline-quality natural gas Compl. ¶18

Key Claims at a Glance

• The complaint asserts independent claims 1 (apparatus), 12 (process), and 34 (process for separating methane and carbon dioxide) Compl. ¶¶19-23
• The essential elements of independent claim 1 include:
  • An apparatus with membrane separation stages and a compressor or vacuum pump.
  • The stages comprise a feed stream separation stage, a retentate separation stage, and a permeate separation stage.
  • The feed stage separates a feed stream into a first permeate and first retentate stream.
  • The retentate stage divides the first retentate stream into a second permeate and second retentate stream, where the second permeate is recycled to the feed stream.
  • The permeate stage divides the first permeate stream into a third retentate and third permeate stream, where the third retentate is recycled to the feed stream.
  • The apparatus is configured not to recompress the first permeate stream.
  • The feed stage membrane module has a mixed gas selectivity of at least 30.
  • The recycled gas volume totals less than 60% of the crude gas stream.
  • The apparatus is configured to increase the concentration of a permeate gas in the feed stream compared to the crude gas stream.
• The complaint expressly reserves the right to assert additional claims Compl. ¶66

U.S. Patent No. 10,471,380 - "Process for separation of gases with reduced maintenance costs"

• Patent Identification: U.S. Patent No. 10,471,380 ("the Priske Patent"), titled "Process for separation of gases with reduced maintenance costs," issued on November 12, 2019.

The Invention Explained

• Problem Addressed: The patent notes that while prior art processes (like those related to the Ungerank Patent) focused on energy optimization, they did not adequately address the need for a solution optimized for lower investment and maintenance costs. This is particularly relevant for facilities where energy is inexpensive, and capital cost is the primary economic driver '380 Patent, col. 4:45-52
• The Patented Solution: The patent discloses a three-stage membrane process that also recycles streams but is configured to reduce capital and maintenance costs, partly by enabling the use of cheaper, less-selective membranes. The key distinguishing features are a higher recycled gas volume (60% to 100% of the crude gas stream), a configuration where the total membrane capacity of the second (retentate) stage is higher than that of the first (feed) stage, and a specified quotient of pressure ratios between the stages '380 Patent, abstract '380 Patent, col. 6:12-36
• Technical Importance: This invention provides an alternative optimization path for membrane separation, prioritizing lower upfront costs over minimal energy use, thereby broadening the economic applicability of the technology.

Key Claims at a Glance

• The complaint asserts independent claim 1 (method) Compl. ¶¶24-26
• The essential elements of independent claim 1 include:
  • A method for separating gases in a three-stage apparatus (feed, retentate, permeate).
  • The method involves separating a feed stream, a first retentate stream, and a first permeate stream in their respective stages.
  • The second permeate stream and third retentate stream are combined with the crude gas stream to form the feed stream.
  • The combined recycled gas volume is from 60% to 100% of the crude gas stream.
  • The total capacity of the membranes in the retentate stage is higher than the total capacity in the feed stream stage.
  • The quotient of the pressure ratio over the permeate stage to the pressure ratio over the feed stage is in a range of from 0.5 to 8.
• The complaint expressly reserves the right to assert additional claims Compl. ¶66

III. The Accused Instrumentality

Product Identification

The complaint identifies two classes of accused instrumentalities: the "Accused Products," which are membrane components manufactured by Defendant Air Products (e.g., PRISM® membranes), and the "Accused Systems," which are three-stage gas-separation systems manufactured and sold by Defendant Greenlane that incorporate the Accused Products Compl. ¶29 Compl. ¶35 Compl. ¶43

Functionality and Market Context

The Accused Systems are alleged to be biogas upgrading systems designed to "cleanse the impurities in biogas and separate the carbon dioxide from the biomethane to create a clean, high-purity low-carbon fuel" Compl. ¶40 The complaint alleges these systems employ a "three stage high efficiency" membrane process to achieve this separation Compl. ¶40 A diagram from Greenlane's materials, included in the complaint, illustrates a three-stage process for biogas upgrading Compl. ¶45 Compl. Exhibit 6 The complaint alleges Air Products is a "global supplier of essential industrial gases and manufacturer of related equipment" and Greenlane is a "global provider of biogas upgrading systems," positioning them as significant market participants Compl. ¶27 Compl. ¶28

IV. Analysis of Infringement Allegations

'038 Patent Infringement Allegations

Claim Element (from Independent Claim 1)	Alleged Infringing Functionality	Complaint Citation	Patent Citation
An apparatus for separating gases, comprising: membrane separation stages; and, a compressor...	The Accused Systems comprise membrane separation stages and a compressor for separating gases.	¶41; ¶44	col. 9:60-65
wherein the membrane separation stages comprise a feed stream separation stage, a retentate separation stage, and a permeate separation stage:	The Accused Systems allegedly comprise three stages identified as a feed stream separation stage, a retentate separation stage, and a permeate separation stage. A diagram provided in the complaint identifies these three stages. (Compl. ¶45, Exhibit 6).	¶45	col. 9:21-31
the feed stream separation stage is configured to separate a feed stream...into a first permeate stream and a first retentate stream,	The feed stream separation stage separates a biogas stream into a first permeate stream and a first retentate stream. An annotated diagram illustrates these streams. (Compl. ¶46, Exhibit 6).	¶46	col. 10:4-7
the retentate separation stage is configured to divide the first retentate stream into a second permeate stream and a second retentate stream, wherein the second permeate stream is supplied to the feed stream...	The retentate separation stage further separates the first retentate stream, with the resulting second permeate stream being recycled back to the feed stream.	¶47	col. 10:11-20
the permeate separation stage is configured to divide the first permeate stream into a third retentate stream and a third permeate stream, wherein the third retentate stream is supplied to the feed stream...	The permeate separation stage further separates the first permeate stream, with the resulting third retentate stream being recycled back to the feed stream.	¶48	col. 10:50-60
the apparatus is configured not to subject the first permeate stream to any recompression,	The Accused Systems allegedly do not recompress the first permeate stream.	¶49	col. 15:52-54
the feed stream separation stage comprises a gas separation membrane module having a mixed gas selectivity of at least 30,	The Accused Products (membranes) are alleged to be available with selectivities that allow the feed stage to have a mixed gas selectivity of at least 30.	¶50	col. 15:55-58
the apparatus is configured such that a gas volume recycled...totals less than 60% by volume of a crude gas stream,	The Accused Systems are alleged to be configured such that the total recycled gas volume is less than 60% of the crude gas stream.	¶51	col. 15:60-63

'380 Patent Infringement Allegations

Claim Element (from Independent Claim 1)	Alleged Infringing Functionality	Complaint Citation	Patent Citation
A method for separating gases from a crude gas stream...in an apparatus comprising a feed stream separation stage, a retentate separation stage and a permeate separation stage...	The Accused Systems are used in a method to separate gases from biogas and comprise three membrane separation stages.	¶53; ¶54	col. 5:55-59
a) a feed stream is separated in the feed stream separation stage into a first permeate stream and a first retentate stream,	The feed stream separation stage separates the feed stream into a first permeate and first retentate stream.	¶57	col. 6:9-11
f) the second permeate stream and the third retentate stream are combined with the crude gas stream to give the feed stream,	The third retentate stream and the second permeate stream are recycled and combined with the crude gas stream. An annotated diagram shows these recycled streams combining to form the feed stream. (Compl. ¶62, Exhibit 6).	¶62	col. 5:2-14
i) the combined gas volume of the second permeate stream and the third retentate stream is from 60 to 100% of the volume of the crude gas stream,	The Accused Systems are allegedly configured such that the combined recycled gas volume is from 60 to 100% of the crude gas stream volume.	¶63	col. 6:15-23
ii) the total capacity of the gas separation membranes in the retentate separation stage is higher than the total capacity...in the feed stream separation stage...	The Accused Systems are allegedly configured such that the total capacity of the membranes in the retentate stage is higher than in the feed stream stage.	¶64	col. 6:24-36
iii) the quotient of the pressure ratio over the permeate separation stage to the pressure ratio over the feed stream separation stage is in a range of from 0.5 to 8.	The Accused Systems are allegedly configured such that the quotient of the pressure ratios between the specified stages is in a range of from 0.5 to 8.	¶65	col. 6:50-54

• Identified Points of Contention:
  • Quantitative Scope: The infringement analysis for both patents may turn on a quantitative factual dispute. The '038 Patent requires a recycled gas volume of "less than 60%," while the '380 Patent requires a volume of "60 to 100%." These numerical ranges appear to be mutually exclusive, raising the question of which, if either, describes the operation of the Accused Systems. The outcome could depend heavily on operational data and measurements obtained during discovery.
  • Technical & Definitional Scope: For the '380 Patent, infringement of the "total capacity" limitation will require both a construction of the term as defined in the patent and technical evidence to prove it. The patent defines "total capacity" based on measurements under specific "standard conditions" '380 Patent, col. 4:53-59 This raises the question of whether Plaintiff can demonstrate, using this specific methodology, that the accused retentate stage's capacity is definitively "higher" than the feed stage's capacity.

V. Key Claim Terms for Construction

U.S. Patent 8,999,038

• The Term: "a gas volume recycled... totals less than 60% by volume of a crude gas stream" (from claim 1).
• Context and Importance: This numerical limitation is a primary feature distinguishing the Ungerank Patent's allegedly energy-optimized process from other configurations, including that of the Priske Patent. The infringement determination may hinge entirely on whether the Accused Systems operate below this 60% threshold.
• Intrinsic Evidence for Interpretation:
  • Evidence for a Broader Interpretation: A party might argue the term should be interpreted based on average or typical operating conditions, rather than being a strict limit that must never be exceeded, though the claim language "totals less than" suggests a firm ceiling.
  • Evidence for a Narrower Interpretation: The claim language presents a clear numerical boundary. The specification reinforces this by framing the invention as an alternative to prior art with different recycling schemes '038 Patent, col. 5:49-63 The fact that this patent underwent reexamination Compl. ¶10 may provide a prosecution history that further defines or narrows the scope of this term.

U.S. Patent 10,471,380

• The Term: "total capacity" (from claim 1).
• Context and Importance: This term is central to one of the '380 Patent's key points of novelty: the relative sizing of the membrane stages to reduce cost. The patent provides an explicit definition: "Membrane capacity... is defined as the product of the membrane surface and the permeance of the membrane at operating temperature that is determined for nitrogen (Grade 4.8) under standard conditions" '380 Patent, col. 4:53-59 Practitioners may focus on this term because the infringement analysis will depend on applying this specific, potentially complex, definition to the Accused Systems.
• Intrinsic Evidence for Interpretation:
  • Evidence for a Broader Interpretation (Plaintiff's likely view): The patent provides its own lexicography, defining "total capacity" in detail. A court would typically hold this definition as controlling, and the analysis would be a factual one of applying the definition to the accused products.
  • Evidence for a Narrower Interpretation (Defendant's potential view): A defendant could argue that ambiguities exist in the definition's parameters (e.g., what constitutes "standard conditions" or how "membrane surface" is precisely measured for the specific accused membranes) to suggest non-infringement. They might argue that the conditions for measuring capacity in the patent are artificial and do not reflect the actual operational characteristics of the accused system.

VI. Other Allegations

• Indirect Infringement: The complaint alleges both induced and contributory infringement against Air Products, and induced infringement against Greenlane. The inducement allegations are based on Defendants allegedly knowing and intending for customers and others to operate the Accused Systems in an infringing manner Compl. ¶69 Compl. ¶70 Compl. ¶80 Compl. ¶81 Contributory infringement is alleged against Air Products for supplying membrane components that are a material part of the invention, are especially adapted for use in the infringing systems, and have no substantial non-infringing use Compl. ¶71 Compl. ¶82 The complaint also pleads infringement under 35 U.S.C. § 271(f)(2) against Air Products for supplying components from the U.S. for combination abroad Compl. ¶72
• Willful Infringement: The complaint alleges willful infringement against both Defendants. The basis for willfulness includes alleged knowledge of the patents since their publication dates and, more specifically for Air Products, knowledge of the Ungerank Patent since at least November 2017, when it allegedly filed an Opposition to the patent's European counterpart Compl. ¶38 Willfulness is also alleged based on knowledge gained upon service of the complaint Compl. ¶75 Compl. ¶85

VII. Analyst's Conclusion: Key Questions for the Case

• A central issue will be a quantitative factual dispute: Do the Accused Systems operate with a recycled gas volume "less than 60%" (implicating the '038 Patent), or in the "60% to 100%" range (implicating the '380 Patent)? The two patents create a sharp, seemingly mutually exclusive boundary, and the case may turn on which side of this line the defendants' technology falls during normal operation.

• A second core issue will be one of claim construction and technical proof for the '380 Patent: Can the term "total capacity," which is explicitly defined by the patentee with reference to specific measurement conditions, be applied to the Accused Systems to prove that the retentate stage's capacity is "higher" than the feed stage's? This will require the court to first accept the patent's definition and then evaluate technical evidence comparing the stages under that specific framework.

• A key question for damages will be willfulness: Does Plaintiff's allegation that Defendant Air Products previously opposed the European counterpart of the '038 Patent establish pre-suit knowledge of the patented technology, thereby exposing the defendants to a finding of willful infringement and the potential for enhanced damages?